Ni(ii)-Catalyzed enantioselective Mukaiyama–Mannich reaction between silyl enol ethers and cyclic N-sulfonyl α-ketiminoesters
Xie, Lei; Ma, Hongli; Li, Jiaqi; Yu, Yuan; Qin, Zhaohai; Fu, Bin; Organic Chemistry Frontiers 4 (2017) 1858–; doi:10.1039/C7QO00370F

data_1553806
_publ_section_title
;
 Ni(ii)-Catalyzed enantioselective Mukaiyama--Mannich reaction between
 silyl enol ethers and cyclic N-sulfonyl \a-ketiminoesters
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1858
_journal_paper_doi               10.1039/C7QO00370F
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 N O5 S'
_chemical_formula_sum            'C22 H19 N O5 S'
_chemical_formula_weight         409.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-12
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2016-12-12 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8173(4)
_cell_length_b                   14.3926(7)
_cell_length_c                   15.3659(7)
_cell_measurement_reflns_used    4140
_cell_measurement_temperature    105.8
_cell_measurement_theta_max      70.8098
_cell_measurement_theta_min      4.2053
_cell_volume                     1949.99(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      105.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -76.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000 -120.0000 25

  2 omega   12.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000 -120.0000 26

  3 omega  -35.00   -9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -180.0000 26

  4 omega  -29.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -56.0000   97.0000 74

  5 omega   59.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -123.0000   44.0000 30

  6 omega   20.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -123.0000 -135.0000 60

  7 omega   19.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  150.0000 46

  8 omega   34.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -148.0000   60.0000 42

  9 omega  108.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 62

 10 omega  115.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 63

 11 omega   63.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 26

 12 omega   91.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

 13 omega   82.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 93

 14 omega   91.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 46

 15 omega  120.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  123.0000  -44.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0168200000
_diffrn_orient_matrix_UB_12      0.0797775000
_diffrn_orient_matrix_UB_13      0.0661894000
_diffrn_orient_matrix_UB_21      -0.1732397000
_diffrn_orient_matrix_UB_22      0.0013106000
_diffrn_orient_matrix_UB_23      0.0130355000
_diffrn_orient_matrix_UB_31      0.0154465000
_diffrn_orient_matrix_UB_32      -0.0713978000
_diffrn_orient_matrix_UB_33      0.0741141000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6453
_diffrn_reflns_theta_full        70.95
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         4.21
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(12)
_refine_ls_extinction_coef       0.0059(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+0.2919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                3629
_reflns_number_total             3678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00370f2.cif
_cod_data_source_block           exp_4697
_cod_original_cell_volume        1950.00(15)
_cod_database_code               1553806
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97