Enantioselective Synthesis of 5,7-Bicyclic Ring Systems from Axially Chiral Allenes Using a Rh(I)-Catalyzed Cyclocarbonylation Reaction
Francois Grillet; Kay M. Brummond; Journal of Organic Chemistry 78 (2013) 3737–3754; doi:10.1021/jo4002432

data_4028153
_publ_section_title
;
 Enantioselective Synthesis of 5,7-Bicyclic Ring Systems from Axially
 Chiral Allenes Using a Rh(I)-Catalyzed Cyclocarbonylation Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3737
_journal_page_last               3754
_journal_paper_doi               10.1021/jo4002432
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H31 N O3 S Si'
_chemical_formula_weight         465.67
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 93.3470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.4022(8)
_cell_length_b                   8.9420(4)
_cell_length_c                   14.2378(6)
_cell_measurement_temperature    150(2)
_cell_volume                     2465.97(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1779
_diffrn_reflns_av_sigmaI/netI    0.1056
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16423
_diffrn_reflns_theta_full        70.05
_diffrn_reflns_theta_max         70.05
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_T_max  0.7323
_exptl_absorpt_correction_T_min  0.6978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.224
_refine_diff_density_min         -1.342
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   4.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4528
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      4.122
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.1340
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3943
_refine_ls_wR_factor_ref         0.3947
_reflns_number_gt                4464
_reflns_number_total             4528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4002432_si_001.cif
_cod_data_source_block           frg2
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4028153