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_4109754
_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            'C31 H37 N O2 Si'
_chemical_formula_weight         483.71
_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                   9.6596(16)
_cell_length_b                   21.302(4)
_cell_length_c                   26.248(4)
_cell_measurement_reflns_used    984
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.46
_cell_volume                     5401.0(16)
_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      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            36172
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      0
_exptl_crystal_description       rod
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0699
_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^)+(0.0672P)^2^+3.8198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                4658
_reflns_number_total             6460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0740420si20070604_115601.cif
_cod_data_source_block           ya58sad
_cod_original_cell_volume        5401.1(16)
_cod_database_code               4109754