Catalytic Asymmetric Mannich Reactions of Glycine Derivatives with Imines. A New Approach to Optically Active α,β-Diamino Acid Derivatives
Luca Bernardi; Aase S. Gothelf; Rita G. Hazell; Karl Anker Jørgensen; Journal of Organic Chemistry 68 (2003) 2583–2591; doi:10.1021/jo026766u

data_4022348
_publ_section_title
;
 Catalytic Asymmetric Mannich Reactions of Glycine Derivatives
 with Imines. A New Approach to Optically Active
 \a,\b-Diamino Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2583
_journal_page_last               2591
_journal_paper_doi               10.1021/jo026766u
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C31 H30 N2 O4 S'
_chemical_formula_weight         526.64
_chemical_name_systematic
;
(2S,3R) Ethyl 2-( (diphenylmethylene)amino)-3-phenyl-3-
(p-toluensulphonylamino) propanoate
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                91.344(4)
_cell_angle_beta                 100.149(4)
_cell_angle_gamma                92.319(4)
_cell_formula_units_Z            4
_cell_length_a                   11.099(1)
_cell_length_b                   15.508(2)
_cell_length_c                   16.210(2)
_cell_measurement_reflns_used    8579
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.5
_cell_volume                     2743(1)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;
       ORTEP-III (Burnett & Johnson,  1996), KRYSTAL
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;
      SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_diffrn_ambient_temperature      120
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21712
_diffrn_reflns_reduction_process 21712
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'XPREP 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       rod
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.5(1)
_refine_diff_density_min         -0.8(1)
_refine_ls_abs_structure_details
; The absolute configuration was determined according to Rogers
(1981) through least squares refinement using all 15695 significant
reflections, including 7355 Bijvoet pairs. The Rogers' factor is 1
for the right chirality, -1 for the wrong hand.
;
_refine_ls_abs_structure_Rogers  1.14(17)
_refine_ls_extinction_coef       170(20)
_refine_ls_extinction_method
;
  Type 1 Lorentzian isotropic ( Becker and Coppens, 1974)
;
_refine_ls_goodness_of_fit_ref   2.13
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     1368
_refine_ls_number_reflns         15695
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.071
_refine_ls_shift/su_max          0.0084
_refine_ls_shift/su_mean         0.0017
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w= 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                15695
_reflns_number_total             18255
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            jo026766usi20030128_124252.cif
_cod_data_source_block           cpd_4b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 152 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4022348