A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines.
Unhale, Rajshekhar A.; Sadhu, Milon M.; Ray, Sumit K.; Biswas, Rayhan G.; Singh, Vinod K.; Chemical communications (Cambridge, England) 54 (2018) 3516–3519; doi:10.1039/C8CC01436A

data_7121399
_publ_section_title
;
 A chiral Br\/onsted acid-catalyzed highly enantioselective Mannich-type
 reaction of \a-diazo esters with in situ generated N-acyl ketimines.
;
_journal_issue                   28
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3516
_journal_page_last               3519
_journal_paper_doi               10.1039/C8CC01436A
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C23 H19 N3 O3 S'
_chemical_formula_weight         417.47
_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
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2018-02-06 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5975(2)
_cell_length_b                   12.0983(2)
_cell_length_c                   19.9600(4)
_cell_measurement_reflns_used    5948
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.863
_cell_measurement_theta_min      2.907
_cell_volume                     2076.14(7)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12106
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.863
_diffrn_reflns_theta_min         2.907
_exptl_absorpt_coefficient_mu    0.186
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1836 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0647P)^2^+0.7048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4563
_reflns_number_total             4933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc01436a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7121399.cif.'
_cod_database_code               7121399
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              53655