Indium-Mediated Asymmetric Intramolecular Allenylation of N-tert-Butanesulfinyl Imines: Efficient and Practical Access to Chiral 3-Allenyl-4-aminochromanes.
Su, Lin; Zhu, Ting-Shun; Xu, Ming-Hua; Organic letters 16 (2014) 4118–4121; doi:10.1021/ol501815e

data_1517233
_publ_section_title
;
 Indium-Mediated Asymmetric Intramolecular Allenylation of
 N-tert-Butanesulfinyl Imines: Efficient and Practical Access to Chiral
 3-Allenyl-4-aminochromanes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4118
_journal_page_last               4121
_journal_paper_doi               10.1021/ol501815e
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration S
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.44
_space_group_IT_number           1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.648(5)
_cell_angle_beta                 106.125(5)
_cell_angle_gamma                95.565(5)
_cell_formula_units_Z            2
_cell_length_a                   7.176(2)
_cell_length_b                   10.859(3)
_cell_length_c                   12.059(4)
_cell_measurement_temperature    296(2)
_cell_volume                     876.2(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15063
_diffrn_reflns_theta_full        27.80
_diffrn_reflns_theta_max         27.80
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9500
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.269
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7673
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.269
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                7026
_reflns_number_total             7673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501815e_si_004.cif
_cod_data_source_block           2013393_0m
_cod_depositor_comments
'Adding full bibliography for 1517232--1517235.cif.'
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1517233