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_4104592
_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            'C17 H14 Br Cl N O2'
_chemical_formula_weight         379.65
_chemical_name_common            4-Bromo-Lactam
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.6070(10)
_cell_angle_beta                 97.4310(10)
_cell_angle_gamma                113.7950(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4375(5)
_cell_length_b                   8.8670(6)
_cell_length_c                   14.4876(10)
_cell_measurement_temperature    153(2)
_cell_volume                     859.87(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_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  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7903
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    2.551
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             382
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          1.493
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.2326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                3282
_reflns_number_total             3902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808811u_si_002.cif
_cod_data_source_block           Lactam124
_cod_database_code               4104592