Organocatalytic Enantioselective Nucleophilic Vinylic Substitution by α-Substituted-α-Cyanoacetates under Phase-Transfer Conditions
Mark Bell; Thomas B. Poulsen; Karl Anker Jørgensen; Journal of Organic Chemistry 72 (2007) 3053–3056; doi:10.1021/jo070024p

data_4022866
_publ_contact_author             'Overgaard, Jacob'
_publ_contact_author_email       jacobo@chem.au.dk
_publ_section_title
;
 Organocatalytic Enantioselective Nucleophilic Vinylic Substitution
 by \a-Substituted-\a-Cyanoacetates under Phase-Transfer Conditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3053
_journal_page_last               3056
_journal_paper_doi               10.1021/jo070024p
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H19 Cl1 N1 O3'
_chemical_formula_sum            'C20 H19 Cl N O3'
_chemical_formula_weight         356.81
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             2006-06-08T21:58:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.641(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1101(2)
_cell_length_b                   16.2044(5)
_cell_length_c                   9.8807(3)
_cell_measurement_reflns_used    4043
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.464
_cell_measurement_theta_min      2.423
_cell_measurement_wavelength     0.71073
_cell_volume                     973.56(5)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13863
_diffrn_reflns_theta_full        25.2
_diffrn_reflns_theta_max         25.2
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                2567
_reflns_number_total             3518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070024prom20070105_044527.cif
_cod_data_source_block           06jo0024
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022866