Aluminum-Catalyzed Enantio- and Diastereoselective Carbonyl Addition of Propargylsilanes. A New Approach to Enantioenriched Vinyl Epoxides
David A. Evans; Yimon Aye; Journal of the American Chemical Society 129 (2007) 9606–9607; doi:10.1021/ja0740420

data_4109755
_publ_contact_author_address
;Department of Chemistry & Chemical Biology
Harvard University
Cambridge MA 02138
;
_publ_contact_author_email       evans@chemistry.harvard.edu
_publ_contact_author_name        'Prof. David A. Evans'
_publ_section_title
;
 Aluminum-Catalyzed Enantio- and Diastereoselective Carbonyl Addition of
 Propargylsilanes. A New Approach to Enantioenriched Vinyl Epoxides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9606
_journal_page_last               9607
_journal_paper_doi               10.1021/ja0740420
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C25 H33 N O2 Si'
_chemical_formula_weight         407.61
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.656(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.094(2)
_cell_length_b                   18.133(3)
_cell_length_c                   10.0075(14)
_cell_measurement_reflns_used    986
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.38
_cell_measurement_theta_min      2.42
_cell_volume                     2423.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.1143
_diffrn_reflns_av_sigmaI/netI    0.2910
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15997
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_meas      0
_exptl_crystal_description       slab
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.664
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.664
_refine_ls_R_factor_all          0.2004
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                1846
_reflns_number_total             5731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0740420si20070604_115624.cif
_cod_data_source_block           ya37
_cod_database_code               4109755