Carbamoyl Anion Addition to N-Sulfinyl Imines: Highly Diastereoselective Synthesis of α-Amino Amides
Jonathan T. Reeves; Zhulin Tan; Melissa A. Herbage; Zhengxu S. Han; Maurice A. Marsini; Zhibin Li; Guisheng Li; Yibo Xu; Keith R. Fandrick; Nina C. Gonnella; Scot Campbell; Shengli Ma; Nelu Grinberg; Heewon Lee; Bruce Z. Lu; Chris H. Senanayake; Journal of the American Chemical Society 135 (2013) 5565–5568; doi:10.1021/ja402647m

data_4119594
_publ_section_title
;
 Carbamoyl Anion Addition to N-Sulfinyl Imines: Highly Diastereoselective
 Synthesis of \a-Amino Amides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5565
_journal_page_last               5568
_journal_paper_doi               10.1021/ja402647m
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C36 H57 Br N3 O3 S'
_chemical_formula_weight         691.82
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 106.3670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.5023(6)
_cell_length_b                   9.8829(2)
_cell_length_c                   15.6531(4)
_cell_measurement_temperature    273(2)
_cell_volume                     3933.71(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15530
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.80
_exptl_absorpt_coefficient_mu    2.184
_exptl_absorpt_correction_T_max  0.9576
_exptl_absorpt_correction_T_min  0.6692
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         5.022
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.188
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6194
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          2.266
_refine_ls_shift/su_mean         0.091
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1522P)^2^+31.4672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2053
_reflns_number_gt                5976
_reflns_number_total             6194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja402647m_si_004.cif
_cod_data_source_block           scan_0m_c2
_cod_database_code               4119594