Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
Susan L. Zultanski; Gregory C. Fu; Journal of the American Chemical Society 133 (2011) 15362–15364; doi:10.1021/ja2079515

data_4106897
_publ_section_title
;
 Catalytic Asymmetric \g-Alkylation of Carbonyl Compounds via
 Stereoconvergent Suzuki Cross-Couplings
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15362
_journal_page_last               15364
_journal_paper_doi               10.1021/ja2079515
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H31 N O'
_chemical_formula_weight         349.50
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 96.082(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.5701(5)
_cell_length_b                   5.6668(2)
_cell_length_c                   20.4694(7)
_cell_measurement_reflns_used    2332
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.00
_cell_measurement_theta_min      4.34
_cell_volume                     2026.59(12)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2010)'
_computing_data_collection       'APEX2 v2010.7.0 (Bruker-AXS, 2010)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2010)'
_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      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Smart APEX2 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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3273
_diffrn_reflns_theta_full        67.77
_diffrn_reflns_theta_max         67.77
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     383
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0779P)^2^+0.9449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                3046
_reflns_number_total             3273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2079515_si_001.cif
_cod_data_source_block           x10032_t4
_cod_database_code               4106897