Diastereoselective Addition of Chlorotitanium Enolate of N-Acyl Thiazolidinethione to O-Methyl Oximes: A Novel, Stereoselective Synthesis of α,β-Disubstituted β-Amino Carbonyl Compounds via Chiral Auxiliary Mediated Azetine Formation
Narendra B. Ambhaikar; James P. Snyder; Dennis C. Liotta; Journal of the American Chemical Society 125 (2003) 3690–3691; doi:10.1021/ja029871u

data_4113612
_publ_section_title
;
 Diastereoselective Addition of Chlorotitanium Enolate of N-Acyl
 Thiazolidinethione to O-Methyl Oximes: A Novel, Stereoselective Synthesis
 of \a,\b-Disubstituted \b-Amino Carbonyl Compounds via Chiral Auxiliary
 Mediated Azetine Formation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3690
_journal_page_last               3691
_journal_paper_doi               10.1021/ja029871u
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C23 H26 N2 O2 S2'
_chemical_formula_weight         426.58
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.9797(2)
_cell_length_b                   19.9201(4)
_cell_length_c                   21.9977(5)
_cell_measurement_reflns_used    7047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.311
_cell_measurement_theta_min      2.994
_cell_volume                     4373.07(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20903
_diffrn_reflns_theta_full        66.29
_diffrn_reflns_theta_max         66.28
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    2.374
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.829608
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      0
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         7471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0716
_reflns_number_gt                7022
_reflns_number_total             7471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja029871usi20030203_094557.cif
_cod_data_source_block           tsc85s
_cod_database_code               4113612