Cobalt(diamine)-Catalyzed Cross-coupling Reaction of Alkyl Halides with Arylmagnesium Reagents: Stereoselective Constructions of Arylated Asymmetric Carbons and Application to Total Synthesis of AH13205
Hirohisa Ohmiya; Hideki Yorimitsu; Koichiro Oshima; Journal of the American Chemical Society 128 (2006) 1886–1889; doi:10.1021/ja057560o

data_4110422
_publ_contact_author             'Hideki Yorimitsu'
_publ_contact_author_email       yori@orgrxn.mbox.media.kyoto-u.ac.jp
_publ_contact_author_fax         +81-75-383-2438
_publ_contact_author_phone       +81-75-383-2441
_publ_section_title
;
 Cobalt(diamine)-Catalyzed Cross-coupling Reaction of Alkyl Halides with
 Arylmagnesium Reagents: Stereoselective Constructions of Arylated
 Asymmetric Carbons and Application to Total Synthesis of AH13205
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1886
_journal_page_last               1889
_journal_paper_doi               10.1021/ja057560o
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_chemical_melting_point          381
_chemical_name_systematic
;
 4-[(1R,2R)-2-{(+)-isomenthoxy}-3-oxacyclopentyl]phenol
;
_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                   5.7150(4)
_cell_length_b                   9.4900(7)
_cell_length_c                   35.349(3)
_cell_measurement_reflns_used    2577
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.041
_cell_measurement_theta_min      2.222
_cell_volume                     1917.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            11661
_diffrn_reflns_theta_full        27.04
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        -2.42
_diffrn_standards_interval_time  195
_diffrn_standards_number         81
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0994
_refine_ls_shift/su_max          2.419
_refine_ls_shift/su_mean         0.094
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2802
_refine_ls_wR_factor_ref         0.3069
_reflns_number_gt                2269
_reflns_number_total             4115
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja057560osi20051104_114853.cif
_cod_data_source_block           1ho
_cod_original_cell_volume        1917.2(2)
_cod_database_code               4110422