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_4105161
_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            'C33.5 H42 Br N3 O3'
_chemical_formula_weight         614.61
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.5010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6331(9)
_cell_length_b                   11.0404(7)
_cell_length_c                   22.0010(15)
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      2.40
_cell_volume                     3233.0(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      170(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            55548
_diffrn_reflns_theta_full        32.10
_diffrn_reflns_theta_max         32.10
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    1.307
_exptl_absorpt_correction_T_max  0.6951
_exptl_absorpt_correction_T_min  0.5609
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1292
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_platon_squeeze_details
; The unit cell contains  6 molecules of pentane which have been treated
as a diffuse contribution to the overall scattering without specific
atom positions by SQUEEZE/PLATON.
;
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         21898
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+0.4476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                13221
_reflns_number_total             21898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9066354_si_003.cif
_cod_data_source_block           ky178s10p
_cod_original_formula_sum        'C33.50 H42 Br N3 O3'
_cod_database_code               4105161