Organocatalyzed Asymmetric Vinylogous Allylic-Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Olefinic Azlactones: Facile Access to Chiral Multifunctional α-Amino Acid Derivatives.
Zhao, Shuai; Zhao, Yuan-Yuan; Lin, Jun-Bing; Xie, Ting; Liang, Yong-Min; Xu, Peng-Fei; Organic letters 17 (2015) 3206–3209; doi:10.1021/acs.orglett.5b01066

data_1520542
_publ_section_title
;
 Organocatalyzed Asymmetric Vinylogous Allylic-Allylic Alkylation of
 Morita-Baylis-Hillman Carbonates with Olefinic Azlactones: Facile Access
 to Chiral Multifunctional \a-Amino Acid Derivatives.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3206
_journal_page_last               3209
_journal_paper_doi               10.1021/acs.orglett.5b01066
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H25 N O4'
_chemical_formula_sum            'C32 H25 N O4'
_chemical_formula_weight         487.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.915(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.62144(14)
_cell_length_b                   20.1343(4)
_cell_length_c                   9.3620(2)
_cell_measurement_reflns_used    4217
_cell_measurement_temperature    293.69(10)
_cell_measurement_theta_max      69.6850
_cell_measurement_theta_min      5.2820
_cell_volume                     1225.54(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  100.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 78

  2 omega  107.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -30.0000 71

  3 omega  107.00  143.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 36

  4 omega   59.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 33

  5 omega   55.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 60

  6 omega   52.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 57

  7 omega   38.00   78.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 40

  8 omega   44.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 39

  9 omega   45.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000  -30.0000 26

 10 omega   51.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 43

 11 omega   59.00  102.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 43

 12 omega   44.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 27

 13 omega   36.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 57

 14 omega   45.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   94.0000 59

 15 omega   35.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 50

 16 omega   37.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 55

 17 omega   36.00  135.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -90.0000 99

 18 omega   30.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  120.0000 90

 19 omega   88.00  158.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 70

 20 omega   60.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 60

 21 omega   21.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -60.0000 34

 22 omega   25.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 27

 23 omega   10.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000 -120.0000 116

 24 omega    6.00   39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 33

 25 omega  -29.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -60.0000 47

 26 omega  -18.00   67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   60.0000 85

 27 omega   23.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  120.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1187395000
_diffrn_orient_matrix_UB_12      0.0585481000
_diffrn_orient_matrix_UB_13      0.0506683000
_diffrn_orient_matrix_UB_21      -0.0903175000
_diffrn_orient_matrix_UB_22      -0.0470331000
_diffrn_orient_matrix_UB_23      0.1015684000
_diffrn_orient_matrix_UB_31      0.1841715000
_diffrn_orient_matrix_UB_32      0.0146888000
_diffrn_orient_matrix_UB_33      0.1231876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8046
_diffrn_reflns_theta_full        69.79
_diffrn_reflns_theta_max         69.79
_diffrn_reflns_theta_min         4.39
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4496
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.0482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                4247
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01066_si_001.cif
_cod_data_source_block           zhaoshuai0122
_cod_depositor_comments          'Adding full bibliography for 1520542.cif.'
_cod_database_code               1520542
_reflns_odcompleteness_completeness 99.87
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2015-01-22
_olex2_submission_special_instructions 'No special instructions were received'