Asymmetric N-Heterocyclic Carbene Catalyzed Addition of Enals to Nitroalkenes: Controlling Stereochemistry via the Homoenolate Reactivity Pathway To Access δ-Lactams
Nicholas A. White; Daniel A. DiRocco; Tomislav Rovis; Journal of the American Chemical Society 135 (2013) 8504–8507; doi:10.1021/ja403847e

data_4119925
_publ_section_title
;
 Asymmetric N-Heterocyclic Carbene Catalyzed Addition of Enals to
 Nitroalkenes: Controlling Stereochemistry via the Homoenolate Reactivity
 Pathway To Access \d-Lactams
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8504
_journal_page_last               8507
_journal_paper_doi               10.1021/ja403847e
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H20 Br N O3 S'
_chemical_formula_sum            'C19 H20 Br N O3 S'
_chemical_formula_weight         422.33
_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                 95.263(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8036(5)
_cell_length_b                   21.9511(18)
_cell_length_c                   14.3746(12)
_cell_measurement_reflns_used    8569
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.34
_cell_volume                     1823.5(3)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'APEX2 (Bruker, 2009)'
_computing_publication_material  'APEX2 (Bruker, 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32881
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    2.387
_exptl_absorpt_correction_T_max  0.8015
_exptl_absorpt_correction_T_min  0.4721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of Gottingen, Germany.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.927
_refine_diff_density_min         -1.456
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         7371
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0281P)^2^+2.2588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                5791
_reflns_number_total             7371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja403847e_si_002.cif
_cod_data_source_block           rovis161
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not determined' was changed to
'?' - the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4119925