Amide Enolate Additions to Acylsilanes: In Situ Generation of Unusual and Stereoselective Homoenolate Equivalents
Robert B. Lettan; Chris V. Galliford; Chase C. Woodward; Karl A. Scheidt; Journal of the American Chemical Society 131 (2009) 8805–8814; doi:10.1021/ja808811u

data_4104593
_publ_contact_author_address
;Department of Chemistry
Northwestern University
215 Sheridan Road
Evanston, IL 60208
;
_publ_contact_author_email       scheidt@northwestern.edu
_publ_contact_author_name        'Karl Scheidt'
_publ_section_title
;
 Amide Enolate Additions to Acylsilanes: In Situ Generation of Unusual and
 Stereoselective Homoenolate Equivalents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8805
_journal_page_last               8814
_journal_paper_doi               10.1021/ja808811u
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C23 H17 Br2 N O3'
_chemical_formula_weight         515.20
_chemical_name_common            'N-bezoyl protected lactam'
_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                 117.0080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.0078(3)
_cell_length_b                   5.54060(10)
_cell_length_c                   14.8626(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1027.71(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      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11869
_diffrn_reflns_theta_full        30.33
_diffrn_reflns_theta_max         30.33
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    3.968
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       flat
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.509
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5027
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          3.593
_refine_ls_shift/su_mean         0.028
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                4166
_reflns_number_total             5027
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808811u_si_003.cif
_cod_data_source_block           Lactam142
_cod_database_code               4104593