Catalytic Enantioselective Hydrophosphonylation of Ketimines Using Cinchona Alkaloids
Shuichi Nakamura; Masashi Hayashi; Yuichi Hiramatsu; Norio Shibata; Yasuhiro Funahashi; Takeshi Toru; Journal of the American Chemical Society 131 (2009) 18240–18241; doi:10.1021/ja908940e

data_4105512
_publ_contact_author_address
;
Department of Frontier Materials
Graduate School of Engineering
Nagoya Inatitute of Technology
Gokiso-cho, Showa-ku
Nagoya 466-8555
Japan
;
_publ_contact_author_email       snakamur@nitech.ac.jp
_publ_contact_author_fax         +81-52-735-5245
_publ_contact_author_name        'Prof. Shuichi Nakamura'
_publ_contact_author_phone       +81-52-735-5245
_publ_section_title
;
 Catalytic Enantioselective Hydrophosphonylation of Ketimines Using
 Cinchona Alkaloids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18240
_journal_page_last               18241
_journal_paper_doi               10.1021/ja908940e
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H29 Cl N O5 P S '
_chemical_formula_sum            'C29 H29 Cl N O5 P S'
_chemical_formula_weight         570.04
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_Int_Tables_number      170
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_audit_creation_date             2009-10-14
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_formula_units_Z            6
_cell_length_a                   15.9700(3)
_cell_length_b                   15.9700(3)
_cell_length_c                   19.0900(5)
_cell_measurement_reflns_used    10502
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      31.2
_cell_measurement_theta_min      2.6
_cell_volume                     4216.44(16)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    Ortep3
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173(1)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rot anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34028
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       prism
_exptl_crystal_F_000             1788.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.37
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3130 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.0029(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6454
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1556
_reflns_number_gt                5704
_reflns_number_total             6454
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja908940e_si_001.cif
_cod_data_source_block           '__S-5'
_cod_original_formula_sum        'C29 H29 Cl N O5 P S '
_cod_database_code               4105512