Rhodium-Catalyzed Asymmetric Reductive Cyclization of Heteroatom-Linked 5-Alkynals with Heteroatom-Substituted Acetaldehydes
Rie Tanaka; Keiichi Noguchi; Ken Tanaka; Journal of the American Chemical Society 132 (2010) 1238–1239; doi:10.1021/ja9104655

data_4101845
_publ_contact_author_address
;
Department of Applied Chemistry
Graduate School of Engineering
Tokyo University of Agriculture and Technology
Koganei
Tokyo 184-8588
Japan
;
_publ_contact_author_email       tanaka-k@cc.tuat.ac.jp
_publ_contact_author_fax         +81-42-388-7037
_publ_contact_author_name        'Dr Ken Tanaka'
_publ_contact_author_phone       +81-42-388-7037
_publ_section_title
;
 Rhodium-Catalyzed Asymmetric Reductive Cyclization of Heteroatom-Linked
 5-Alkynals with Heteroatom-Substituted Acetaldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1238
_journal_page_last               1239
_journal_paper_doi               10.1021/ja9104655
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H43 N O5 S'
_chemical_formula_sum            'C31 H43 N O5 S'
_chemical_formula_weight         541.72
_chemical_name_systematic
;
 (S)-(+)-Benzyloxyacetic acid 1-(toluene-4-sulfonyl)-4
 -undecylidenepyrrolidin-3-yl ester
;
_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             2009-10-02
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.142(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8993(5)
_cell_length_b                   5.32220(19)
_cell_length_c                   21.5004(9)
_cell_measurement_reflns_used    14262
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.3
_cell_volume                     1519.84(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23641
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881  2214 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0133(11)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0658
_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^)+(0.0937P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1985
_reflns_number_gt                2862
_reflns_number_total             5308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9104655_si_001.cif
_cod_data_source_block           I
_cod_original_cell_volume        1519.83(10)
_cod_database_code               4101845