Stereoselective synthesis of beta-substituted beta-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines.
Velázquez, Francisco; Arasappan, Ashok; Chen, Kevin; Sannigrahi, Mousumi; Venkatraman, Srikanth; McPhail, Andrew T.; Chan, Tze-Ming; Shih, Neng-Yang; Njoroge, F. George; Organic letters 8 (2006) 789–792; doi:10.1021/ol053132b

data_1505873
_publ_section_title
;
 Stereoselective synthesis of beta-substituted beta-amino sulfones and
 sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              789
_journal_page_last               792
_journal_paper_doi               10.1021/ol053132b
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C18 H31 N O3 S2'
_chemical_formula_sum            'C18 H31 N O3 S2'
_chemical_formula_weight         373.58
_chemical_name_common            'compound 16'
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   calc
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.435(1)
_cell_length_b                   11.465(1)
_cell_length_c                   19.104(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      40.00
_cell_measurement_theta_min      36.00
_cell_volume                     2066.5(4)
_computing_cell_refinement
' CELDIM in CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_structure_refinement  'maXus (Mackay et al., 1999)'
_computing_structure_solution    'maXus (Mackay et al., 1999)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2428
_diffrn_reflns_theta_full        74.73
_diffrn_reflns_theta_max         74.73
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        'no decay, variation <1.0%'
_diffrn_standards_interval_time  120
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    2.451
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_preparation       'mounted on thin glass fiber'
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.73
_refine_ls_extinction_coef       21E4(5)
_refine_ls_extinction_expression
;
 equation (22) p 292 'Crystallographic Computing' (1970)
 coefficient is multip[lied by 10^4
;
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_all   1.02
_refine_ls_goodness_of_fit_gt    1.02
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.064
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     'w=1/[\s^2^(Fo)+ 0.11000(Fo^2^)']'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.166
_refine_ls_wR_factor_gt          0.162
_reflns_d_resolution_high        0.63
_reflns_d_resolution_low         2.21
_reflns_number_gt                2165
_reflns_number_total             2428
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol053132bsi20051226_012437.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1505873
_exptl_crystal_solvent           't-butyl methyl ether'
_refine_ls_number_reflections    2165
_refine_ls_number_of_parameters  219
_refine_ls_number_contraints     31
_refine_ls_absolute_structure_rogers +1.21(9)