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_4113611
_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            'C16 H20 N2 S2'
_chemical_formula_weight         304.46
_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            4
_cell_length_a                   5.7624(9)
_cell_length_b                   12.2485(19)
_cell_length_c                   22.486(4)
_cell_measurement_reflns_used    7259
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.816
_cell_measurement_theta_min      3.185
_cell_volume                     1587.1(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22610
_diffrn_reflns_theta_full        28.84
_diffrn_reflns_theta_max         28.84
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        <2%"
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.815490
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                3987
_reflns_number_total             4156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja029871usi20030203_094556.cif
_cod_data_source_block           na243s
_cod_database_code               4113611