Tandem Asymmetric Aza-Darzens/Ring-Opening Reactions: Dual Functionality from the Silane Lewis Acid
S. Corey Valdez; James L. Leighton; Journal of the American Chemical Society 131 (2009) 14638–14639; doi:10.1021/ja9066354

data_4105159
_publ_section_title
;
 Tandem Asymmetric Aza-Darzens/Ring-Opening Reactions: Dual Functionality
 from the Silane Lewis Acid
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14638
_journal_page_last               14639
_journal_paper_doi               10.1021/ja9066354
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H19 Cl N2 O3'
_chemical_formula_weight         346.80
_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            8
_cell_length_a                   8.1452(6)
_cell_length_b                   17.3379(12)
_cell_length_c                   24.3640(17)
_cell_measurement_reflns_used    9312
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.35
_cell_volume                     3440.7(4)
_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      125(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            55460
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9648
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            PLATE
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       COLORLESS
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         10535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0540
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1595
_reflns_number_gt                8506
_reflns_number_total             10535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9066354_si_001.cif
_cod_data_source_block           ky79s10
_cod_database_code               4105159