Cobalt-Mediated, Enantioselective Synthesis of C2 and C1 Dienes
W. Christopher Boyd; Mark R. Crimmin; Lauren E. Rosebrugh; Jennifer M. Schomaker; Robert G. Bergman; F. Dean Toste; Journal of the American Chemical Society 132 (2010) 16365–16367; doi:10.1021/ja107968c

data_4103563
_publ_section_title
;
 Cobalt-Mediated, Enantioselective Synthesis of C2 and C1 Dienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16365
_journal_page_last               16367
_journal_paper_doi               10.1021/ja107968c
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H24 O2'
_chemical_formula_weight         284.38
_chemical_name_common            'compound RRRR14b'
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.995(2)
_cell_angle_beta                 85.672(2)
_cell_angle_gamma                74.704(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4289(2)
_cell_length_b                   9.9793(3)
_cell_length_c                   12.8331(4)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      67.32
_cell_measurement_theta_min      3.48
_cell_volume                     785.77(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15489
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.60
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5016
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.1233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                4848
_reflns_number_total             5016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja107968c_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4103563