Enantioselective Synthesis of Alkyne-Substituted Quaternary Carbon Stereogenic Centers through NHC-Cu-Catalyzed Allylic Substitution Reactions with (i-Bu)2(Alkynyl)aluminum Reagents
Jennifer A. Dabrowski; Fang Gao; Amir H. Hoveyda; Journal of the American Chemical Society 133 (2011) 4778–4781; doi:10.1021/ja2010829

data_4105892
_publ_section_title
;
 Enantioselective Synthesis of Alkyne-Substituted Quaternary Carbon
 Stereogenic Centers through NHC-Cu-Catalyzed Allylic Substitution
 Reactions with (i-Bu)2(Alkynyl)aluminum Reagents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4778
_journal_page_last               4781
_journal_paper_doi               10.1021/ja2010829
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 O2'
_chemical_formula_sum            'C19 H20 O2'
_chemical_formula_weight         280.35
_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                   6.5385(3)
_cell_length_b                   11.8940(6)
_cell_length_c                   19.4196(9)
_cell_measurement_reflns_used    8205
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      65.58
_cell_measurement_theta_min      4.36
_cell_volume                     1510.24(12)
_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      143(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Kappa APEX II DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9239
_diffrn_reflns_theta_full        65.58
_diffrn_reflns_theta_max         65.58
_diffrn_reflns_theta_min         4.36
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.8855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     na
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.2433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                2428
_reflns_number_total             2479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2010829_si_001.cif
_cod_data_source_block           C19H20O2
_cod_database_code               4105892