Highly Diastereoselective Synthesis of Homoallylic Alcohols Bearing Adjacent Quaternary Centers Using Substituted Allylic Zinc Reagents
Hongjun Ren; Guillaume Dunet; Peter Mayer; Paul Knochel; Journal of the American Chemical Society 129 (2007) 5376–5377; doi:10.1021/ja071380s

data_4109367
_publ_section_title
;
 Highly Diastereoselective Synthesis of Homoallylic Alcohols Bearing
 Adjacent Quaternary Centers Using Substituted Allylic Zinc Reagents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5376
_journal_page_last               5377
_journal_paper_doi               10.1021/ja071380s
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C22 H22 Br N3 O'
_chemical_formula_weight         424.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.641(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.4586(4)
_cell_length_b                   20.9241(10)
_cell_length_c                   13.0389(5)
_cell_measurement_temperature    200(2)
_cell_volume                     3943.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28647
_diffrn_reflns_theta_full        24.27
_diffrn_reflns_theta_max         24.27
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    2.102
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             1744
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         6290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0065P)^2^+3.8086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                4381
_reflns_number_total             6290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071380ssi20070302_065626.cif
_cod_data_source_block           kn341
_cod_database_code               4109367