Enantioselective synthesis of chiral α,β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines.
Wang, Zhen-Hua; Wu, Zhi-Jun; Yue, Deng-Feng; You, Yong; Xu, Xiao-Ying; Zhang, Xiao-Mei; Yuan, Wei-Cheng; Organic & biomolecular chemistry 14 (2016) 6568–6576; doi:10.1039/c6ob01191h

data_7155153
_publ_section_title
;
 Enantioselective synthesis of chiral \a,\b-unsaturated \g-substituted
 butyrolactams by organocatalyzed direct asymmetric vinylogous Michael
 addition of \a,\b-unsaturated \g-butyrolactam to 2-enoylpyridines.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6568
_journal_page_last               6576
_journal_paper_doi               10.1039/c6ob01191h
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H22 N2 O4 S'
_chemical_formula_weight         398.46
_chemical_name_systematic
'(S)-tert-butyl 2-oxo-5-((R)-3-oxo-1-phenyl-3-(pyridin-2-yl)propyl)-2,5-dihydro-1H-pyrrole-1-carboxylate'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-11-03 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.291(5)
_cell_length_b                   10.918(5)
_cell_length_c                   22.462(5)
_cell_measurement_reflns_used    3814
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.6409
_cell_measurement_theta_min      3.9327
_cell_volume                     2033.3(16)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5986
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.770
_diffrn_reflns_theta_min         3.936
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ????
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1221 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.058(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0546P)^2^+0.9243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                3228
_reflns_number_total             3612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01191h2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7155153.cif.'
_cod_database_code               7155153
_shelx_estimated_absorpt_t_min   0.542
_shelx_estimated_absorpt_t_max   0.594
_shelxl_version_number           2013-4
_shelx_res_checksum              81910