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_7118342
_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_formula_moiety         'C42 H57 N2 O4 P Si, 0.5(H2 O)'
_chemical_formula_sum            'C42 H58 N2 O4.5 P Si'
_chemical_formula_weight         721.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-29
_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                85.201(5)
_cell_angle_beta                 86.909(5)
_cell_angle_gamma                86.437(5)
_cell_formula_units_Z            2
_cell_length_a                   11.473(4)
_cell_length_b                   13.299(5)
_cell_length_c                   13.766(5)
_cell_measurement_reflns_used    1081
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.49
_cell_measurement_theta_min      2.22
_cell_volume                     2086.5(13)
_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 0.983
_diffrn_measured_fraction_theta_max 0.955
_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  0.0449
_diffrn_reflns_av_unetI/netI     0.1281
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12527
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.217
_diffrn_reflns_theta_min         2.052
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9145
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0557 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.9145.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             778
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.189
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0045(17)
_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   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         8916
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.0750
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1240P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.2528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3645
_reflns_number_total             8916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc08118a2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2086.5(12)
_cod_original_formula_sum        'C42 H58 N2 O4.50 P Si'
_cod_database_code               7118342
_olex2_refinement_description
;
1. 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,H) groups
2. Uiso/Uaniso restraints and constraints
C29: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C28 \\sim C29 \\sim C30 \\sim C31: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
3. Others
 Fixed Sof: O5(0.5) H5A(0.5) H5B(0.5)
4.a Riding coordinates:
 N1(H1)
4.b Free rotating group:
 O5(H5A,H5B)
4.c Ternary CH refined with riding coordinates:
 C13(H13)
4.d Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C35(H35A,H35B)
4.e Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26),
  C27(H27)
4.f Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              30841
_shelx_hkl_checksum              91346
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'