Intriguing Behavior of Cinchona Alkaloids in the Enantioselective Organocatalytic Hydroxyamination of α-Substituted-α-cyanoacetates
Jesús López-Cantarero; M. Belén Cid; Thomas B. Poulsen; Marco Bella; José Luis García Ruano; Karl Anker Jørgensen; Journal of Organic Chemistry 72 (2007) 7062–7065; doi:10.1021/jo071186o

data_4024152
_publ_contact_author             'Farrugia, Louis J.'
_publ_contact_author_email       louis@chem.gla.ac.uk
_publ_section_title
;
 Intriguing Behavior of Cinchona Alkaloids in the Enantioselective
 Organocatalytic Hydroxyamination of \a-Substituted-\a-cyanoacetates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7062
_journal_page_last               7065
_journal_paper_doi               10.1021/jo071186o
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H20 N2 O2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_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             2007-05-14T10:49:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.906(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0966(2)
_cell_length_b                   15.7561(7)
_cell_length_c                   8.7435(3)
_cell_measurement_reflns_used    1806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.06
_cell_measurement_theta_min      5.21
_cell_measurement_wavelength     0.71073
_cell_volume                     815.27(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      100(2)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7566
_diffrn_reflns_theta_full        64
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         5.21
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1158 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0406(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.0600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                2481
_reflns_number_total             2568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo071186o-File002.cif
_cod_data_source_block           07jo0016cu_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024152
_refine_friedel_coverage         0.821