Bisphosphine-Catalyzed Mixed Double-Michael Reactions: Asymmetric Synthesis of Oxazolidines, Thiazolidines, and Pyrrolidines
Vardhineedi Sriramurthy; Gregg A. Barcan; Ohyun Kwon; Journal of the American Chemical Society 129 (2007) 12928–12929; doi:10.1021/ja073754n

data_4110097
_publ_section_title
;
 Bisphosphine-Catalyzed Mixed Double-Michael Reactions: Asymmetric
 Synthesis of Oxazolidines, Thiazolidines, and Pyrrolidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12928
_journal_page_last               12929
_journal_paper_doi               10.1021/ja073754n
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H23 N O5 S'
_chemical_formula_sum            'C16 H23 N O5 S'
_chemical_formula_weight         341.41
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.912(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.149(4)
_cell_length_b                   9.248(4)
_cell_length_c                   11.916(5)
_cell_measurement_temperature    298(2)
_cell_volume                     889.5(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8582
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.8688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       platelet
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     271
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.0644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                4580
_reflns_number_total             4871
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja073754nsi20070524_095736.cif
_cod_data_source_block           kw107bs
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4110097