Carbamoyl anion-initiated cascade reaction for stereoselective synthesis of substituted α-hydroxy-β-amino amides.
Lin, Chao-Yang; Ma, Peng-Ju; Sun, Zhao; Lu, Chong-Dao; Xu, Yan-Jun; Chemical communications (Cambridge, England) 52 (2016) 912–915; doi:10.1039/c5cc08118a

data_7118343
_publ_section_title
;
 Carbamoyl anion-initiated cascade reaction for stereoselective synthesis
 of substituted \a-hydroxy-\b-amino amides.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              912
_journal_page_last               915
_journal_paper_doi               10.1039/c5cc08118a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H31 Br N2 O3 S'
_chemical_formula_sum            'C24 H31 Br N2 O3 S'
_chemical_formula_weight         507.48
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-28 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.891(13)
_cell_length_b                   16.14(2)
_cell_length_c                   16.21(2)
_cell_measurement_reflns_used    1277
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.88
_cell_measurement_theta_min      2.41
_cell_volume                     2588(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.1660
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15227
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.179
_diffrn_reflns_theta_min         2.412
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8412.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5656
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.1860
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1054P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.2260
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2281
_reflns_number_total             5656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc08118a2.cif
_cod_data_source_block           123
_cod_database_code               7118343
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.99(2) 0.01(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C13-C18 = C17-C16 = C15-C14
 1.4 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              30528
_shelx_hkl_checksum              34340
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'