Stereoselective α-Aminoallylation of Aldehydes with Chiraltert-Butanesulfinamides and Allyl Bromides
José C. González-Gómez; Mohamed Medjahdi; Francisco Foubelo; Miguel Yus; Journal of Organic Chemistry 75 (2010) 6308–6311; doi:10.1021/jo101379u

data_4025685
_publ_section_title
;
 Stereoselective \a-Aminoallylation of Aldehydes with
 Chiraltert-Butanesulfinamides and Allyl Bromides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6308
_journal_page_last               6311
_journal_paper_doi               10.1021/jo101379u
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H28 N O S'
_chemical_formula_sum            'C18 H28 N O S'
_chemical_formula_weight         306.47
_chemical_name_systematic
;
?
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.447(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3449(8)
_cell_length_b                   17.133(3)
_cell_length_c                   10.4547(15)
_cell_measurement_reflns_used    28.71
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      22.75
_cell_measurement_theta_min      2.3
_cell_volume                     931.1(3)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics
;
'SHELXTL Rel. 6.12/V (Siemens,
1996)'
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7828
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.5548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s2^(Fo2^)+(0.0247P)2^+0.0905P] where P=(Fo2^+2Fc2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2982
_reflns_number_total             3266
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo101379u_si_001.cif
_cod_data_source_block           x
_cod_original_cell_volume        931.1(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025685