Asymmetric enamine catalysis with β-ketoesters by chiral primary amine: divergent stereocontrol modes.
Xu, Changming; Zhang, Long; Luo, Sanzhong; The Journal of organic chemistry 79 (2014) 11517–11526; doi:10.1021/jo502152w

data_4030167
_publ_section_title
;
 Asymmetric enamine catalysis with \b-ketoesters by chiral primary amine:
 divergent stereocontrol modes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11517
_journal_page_last               11526
_journal_paper_doi               10.1021/jo502152w
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H21 Br N2 O3'
_chemical_formula_sum            'C18 H21 Br N2 O3'
_chemical_formula_weight         393.28
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.871(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.425(2)
_cell_length_b                   29.523(7)
_cell_length_c                   8.348(2)
_cell_measurement_reflns_used    6095
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.07
_cell_volume                     1741.7(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 Ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 Ver 1.1'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19312
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    2.379
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7854
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0291P)^2^+0.2114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                7447
_reflns_number_total             7854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502152w_si_002.cif
_cod_data_source_block           mx2722
_cod_depositor_comments          'Adding full bibliography for 4030167.cif.'
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4030167