Highly Enantioselective Rh-Catalyzed Carboacylation of Olefins: Efficient Syntheses of Chiral Poly-Fused Rings
Tao Xu; Haye Min Ko; Nikolas A. Savage; Guangbin Dong; Journal of the American Chemical Society 134 (2012) 20005–20008; doi:10.1021/ja309978c

data_4118998
_publ_section_title
;
 Highly Enantioselective Rh-Catalyzed Carboacylation of Olefins: Efficient
 Syntheses of Chiral Poly-Fused Rings
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20005
_journal_page_last               20008
_journal_paper_doi               10.1021/ja309978c
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 Br O3'
_chemical_formula_sum            'C19 H17 Br O3'
_chemical_formula_weight         373.24
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.220(2)
_cell_length_b                   12.634(5)
_cell_length_c                   24.533(10)
_cell_measurement_reflns_used    7748
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.0
_cell_volume                     1617.9(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1739
_diffrn_reflns_av_sigmaI/netI    0.2544
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7689
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    2.553
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_coef       0.0037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1939
_refine_ls_R_factor_gt           0.0776
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0038P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1220
_reflns_number_total             2691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja309978c_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4118998