Aromatic Heterocycles as Activating Groups for Asymmetric Conjugate Addition Reactions. Enantioselective Copper-Catalyzed Reduction of 2-Alkenylheteroarenes
Leszek Rupnicki; Aakarsh Saxena; Hon Wai Lam; Journal of the American Chemical Society 131 (2009) 10386–10387; doi:10.1021/ja904365h

data_4104787
_publ_contact_author_email       f.j.white@sms.ed.ac.uk
_publ_contact_author_name        'Fraser J. White'
_publ_section_title
;
 Aromatic Heterocycles as Activating Groups for Asymmetric Conjugate
 Addition Reactions. Enantioselective Copper-Catalyzed Reduction of
 2-Alkenylheteroarenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10386
_journal_page_last               10387
_journal_paper_doi               10.1021/ja904365h
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        'Leszek Rupnicki'
_chemical_formula_moiety         'C12 H14 N O, C7 H7 S O3'
_chemical_formula_sum            'C19 H21 N O4 S'
_chemical_formula_weight         359.43
_space_group_IT_number           1
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_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.205(3)
_cell_angle_beta                 100.064(3)
_cell_angle_gamma                90.673(4)
_cell_formula_units_Z            4
_cell_length_a                   6.7723(4)
_cell_length_b                   14.7754(9)
_cell_length_c                   18.9647(10)
_cell_measurement_reflns_used    8356
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.27
_cell_volume                     1748.15(18)
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
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_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16643
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.6946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'CHCl3 layered with Et2O'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.435
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     902
_refine_ls_number_reflns         11342
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+2.2454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1762
_reflns_number_gt                10154
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja904365h_si_002.cif
_cod_data_source_block           hl9004
_cod_original_cell_volume        1748.15(17)
_cod_database_code               4104787