Palladium-Catalyzed Enantioselective α-Arylation and α-Vinylation of Oxindoles Facilitated by an Axially Chiral P-Stereogenic Ligand
Alexander M. Taylor; Ryan A. Altman; Stephen L. Buchwald; Journal of the American Chemical Society 131 (2009) 9900–9901; doi:10.1021/ja903880q

data_4104727
_publ_contact_author
;
Stephen L. Buchwald
Department of Chemistry
Massachusetts Institute of Technology
77 Massachusetts Avenue
Cambridge, MA 02139 

;
_publ_contact_author_email       sbuchwal@mit.edu
_publ_contact_author_fax         '(617) 253-3297'
_publ_contact_author_phone       '(617) 253-1885'
_publ_section_title
;
 Palladium-Catalyzed Enantioselective \a-Arylation and \a-Vinylation of
 Oxindoles Facilitated by an Axially Chiral P-Stereogenic Ligand
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9900
_journal_page_last               9901
_journal_paper_doi               10.1021/ja903880q
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H15 N O'
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.9340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3945(3)
_cell_length_b                   17.4160(6)
_cell_length_c                   8.8582(3)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      2.54
_cell_volume                     1140.63(7)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 2009)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 2009)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2009)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'phi and omega 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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15919
_diffrn_reflns_theta_full        68.59
_diffrn_reflns_theta_max         68.59
_diffrn_reflns_theta_min         4.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.9027
_exptl_absorpt_correction_T_min  0.7680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3991
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0479P)^2^+0.2052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                3981
_reflns_number_total             3991
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903880q_si_002.cif
_cod_data_source_block           amt1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4104727