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_4119593
_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_absolute_configuration ad
_chemical_formula_moiety         '2(C18 H30 N2 O2 S), 0.5(C6)'
_chemical_formula_sum            'C39 H60 N4 O4 S2'
_chemical_formula_weight         713.07
_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'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3958(3)
_cell_length_b                   17.6638(6)
_cell_length_c                   26.0979(8)
_cell_volume                     4331.4(2)
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9961
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            34105
_diffrn_reflns_theta_full        66.6995
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_min         5.00
_exptl_absorpt_coefficient_mu    1.422
_exptl_crystal_density_diffrn    1.0934
_exptl_crystal_F_000             1550.8187
_refine_diff_density_max         0.8212
_refine_diff_density_min         -0.2784
_refine_diff_density_rms         0.0955
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.000(15)
_refine_ls_d_res_high            0.8393
_refine_ls_d_res_low             8.8403
_refine_ls_goodness_of_fit_ref   1.0609
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    84
_refine_ls_number_parameters     467
_refine_ls_number_reflns         7637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0609
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.0747
_refine_ls_shift/su_mean         0.0030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1046P)^2^+1.7877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.992
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              -20
_reflns_limit_l_max              31
_reflns_limit_l_min              -30
_reflns_number_gt                7268
_reflns_number_total             7637
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja402647m_si_003.cif
_cod_data_source_block           scan_0m_P212121
_cod_database_code               4119593
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H6 of C6, H7 of C7, H5 of C5, H23 of C23, H31 of C31, H30 of
  C30, H24 of C24, H22 of C22, H13 of C13
 At 1.5 times of:
  {H10a,H10b,H10c} of C10, {H15a,H15b,H15c} of C15, {H11a,H11b,H11c} of C11,
  {H27a,H27b,H27c} of C27, {H16a,H16b,H16c} of C16, {H33a,H33b,H33c} of C33,
  {H18a,H18b,H18c} of C18, {H34a,H34b,H34c} of C34, {H17a,H17b,H17c} of C17,
  {H28a,H28b,H28c} of C28, {H25a,H25b,H25c} of C25, {H8a,H8b,H8c} of C8, {H9a,
  H9b,H9c} of C9, {H29a,H29b,H29c} of C29, {H35a,H35b,H35c} of C35, {H1a,H1b,
  H1c} of C1
2. others
 Fixed Sof: C36(0.5) C0aa(0.5) C1aa(0.5) C2aa(0.5) C3aa(0.5) C4aa(0.5)
 H36b(0.5) H1aa(0.5) H1ab(0.5) H1aa(0.5) H3aa(0.5) H36a(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C22(H22), C23(H23), C24(H24),
 C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c),
 C11(H11a,H11b,H11c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,
 H17c), C18(H18a,H18b,H18c), C25(H25a,H25b,H25c), C27(H27a,H27b,H27c), C28(H28a,
 H28b,H28c), C29(H29a,H29b,H29c), C33(H33a,H33b,H33c), C34(H34a,H34b,H34c),
 C35(H35a,H35b,H35c)
;