Highly Enantio- and Diastereoselective One-Pot Methods for the Synthesis of Halocyclopropyl Alcohols
Hun Young Kim; Luca Salvi; Patrick J. Carroll; Patrick J. Walsh; Journal of the American Chemical Society 131 (2009) 954–962; doi:10.1021/ja806989n

data_4103793
_publ_section_title
;
 Highly Enantio- and Diastereoselective One-Pot Methods for the Synthesis
 of Halocyclopropyl Alcohols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              954
_journal_page_last               962
_journal_paper_doi               10.1021/ja806989n
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C23 H29.5 Br0.5 O4'
_chemical_formula_weight         409.92
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.774(15)
_cell_angle_beta                 89.559(16)
_cell_angle_gamma                77.542(18)
_cell_formula_units_Z            2
_cell_length_a                   7.2994(18)
_cell_length_b                   12.819(3)
_cell_length_c                   13.121(3)
_cell_measurement_temperature    153(1)
_cell_volume                     1170.7(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      153(1)
_diffrn_measured_fraction_theta_full 0.827
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9188
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8604
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             434
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.315(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         9188
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+2.6040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.1881
_reflns_number_gt                8217
_reflns_number_total             9188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806989n_si_005.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 1 '
_cod_original_formula_sum        'C23 H29.50 Br0.50 O4'
_cod_database_code               4103793