Nickel(II)-Catalyzed Enantioselective α-Vinylation of β-Keto Amides/Esters with Hypervalent Iodine Salts.
Guo, Jing; Lin, Lili; Liu, Yangbin; Li, Xiangqiang; Liu, Xiaohua; Feng, Xiaoming; Organic letters 18 (2016) 5540–5543; doi:10.1021/acs.orglett.6b02785

data_1555870
_publ_section_title
;
 Nickel(II)-Catalyzed Enantioselective \a-Vinylation of \b-Keto
 Amides/Esters with Hypervalent Iodine Salts.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5540
_journal_page_last               5543
_journal_paper_doi               10.1021/acs.orglett.6b02785
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                115.442(7)
_cell_angle_beta                 109.848(6)
_cell_angle_gamma                92.591(5)
_cell_formula_units_Z            1
_cell_length_a                   7.0663(4)
_cell_length_b                   8.3624(5)
_cell_length_c                   8.9048(7)
_cell_measurement_reflns_used    4838
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.6270
_cell_measurement_theta_min      6.0820
_cell_volume                     435.48(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

  2 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -120.0000 94

  3 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 88

  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   90.0000 67

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  120.0000 74

  7 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000    0.0000 74

  8 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000    0.0000 101

  9 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -30.0000 84

 10 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -120.0000 84

 11 omega    5.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   88.0000  -53.8339 28

 12 omega    4.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   90.0000 -111.3124 28

 13 omega   12.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   83.0000   26.1602 28

 14 omega   12.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   83.0000  -48.6692 28

 15 omega   14.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   80.0000 -178.6152 32

 16 omega   16.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000  154.9354 29

 17 omega   18.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000  -10.1554 28

 18 omega   18.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000  -34.7251 28

 19 omega   16.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000  115.7354 29

 20 omega   25.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   74.0000   87.4508 92

 21 omega   24.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   76.0000  126.1041 93

 22 omega   27.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -117.3702 95

 23 omega   29.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   74.0000   34.3303 92

 24 omega   37.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000 -171.9716 92

 25 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 26 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

 27 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85

 28 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 29 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 30 omega   39.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 31 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 32 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 95

 33 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

 34 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 35 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 85

 36 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 37 omega   39.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 38 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 39 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 40 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 41 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 42 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 43 omega   87.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 44 omega   81.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 45 omega   40.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 95

 46 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 47 omega   39.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 48 omega   90.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

 49 omega   90.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 29

 50 omega   82.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0880452000
_diffrn_orient_matrix_UB_12      -0.2027353000
_diffrn_orient_matrix_UB_13      -0.0717749000
_diffrn_orient_matrix_UB_21      0.1815868000
_diffrn_orient_matrix_UB_22      -0.0491132000
_diffrn_orient_matrix_UB_23      -0.0562770000
_diffrn_orient_matrix_UB_31      0.1259754000
_diffrn_orient_matrix_UB_32      0.0180438000
_diffrn_orient_matrix_UB_33      0.1878637000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8385
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.917
_diffrn_reflns_theta_min         5.998
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description
;
;
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1120P)^2^+0.0082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.796
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                3005
_reflns_number_total             3052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02785_si_003.cif
_cod_data_source_block           fxm-bz-2-ph-2
_cod_original_cell_volume        435.48(5)
_cod_database_code               1555870
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C009(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00B(H00c), C00C(H00d), C00D(H00e), C00E(H00f), C00F(H00g),
 C00G(H00h), C00I(H00I), C00J(H00J), C00K(H00K)
2.c Idealised Me refined as rotating group:
 C00L(H00l,H00m,H00n), C00M(H00o,H00p,H00q), C00N(H00r,H00s,H00t)
;
_shelx_res_checksum              14827
_shelx_hkl_checksum              55817
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-09
_olex2_submission_special_instructions 'No special instructions were received'