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_4109756
_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            'C30 H35 N O2 Si'
_chemical_formula_weight         469.68
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   9.5087(17)
_cell_length_b                   21.076(4)
_cell_length_c                   26.118(5)
_cell_measurement_temperature    293(2)
_cell_volume                     5234.2(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0970
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            35328
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.116
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             2016
_refine_diff_density_max         1.179
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0781
_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^)+(0.0805P)^2^+4.9497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.2004
_reflns_number_gt                4103
_reflns_number_total             6241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0740420si20070604_115643.cif
_cod_data_source_block           ya59sad
_cod_original_cell_volume        5234.2(16)
_cod_database_code               4109756