Asymmetric synthesis of δ-amino acid derivatives via diastereoselective vinylogous Mannich reactions between N-tert-butanesulfinyl imines and dioxinone-derived lithium dienolate
Li, Guijun; Xu, Xiaoliang; Tian, Hongchang; Liu, Xiaotong; Chen, Wen; Yang, Xiaodong; Zhang, Hongbin; RSC Advances 7 (2017) 50822–; doi:10.1039/C7RA10529K

data_7229475
_publ_section_title
;
 Asymmetric synthesis of \d-amino acid derivatives via diastereoselective
 vinylogous Mannich reactions between N-tert-butanesulfinyl imines and
 dioxinone-derived lithium dienolate
;
_journal_issue                   80
_journal_name_full               'RSC Advances'
_journal_page_first              50822
_journal_paper_doi               10.1039/C7RA10529K
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H25 N O4 S'
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_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-09-09 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   11.366(8)
_cell_length_c                   16.422(11)
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.8903
_cell_measurement_theta_min      2.4805
_cell_volume                     1969(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.976
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
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_diffrn_reflns_number            11219
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.179
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       PLATE
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_exptl_crystal_size_max          0.330
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_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 541 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3469
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_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1814
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra10529k2.cif
_cod_data_source_block           1_CCDC2
_cod_database_code               7229475
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.973
_shelxl_version_number           2014-3
_shelx_res_checksum              28094