Enantioselective Synthesis of Axially Chiral Hydroxy Carboxylic Acid Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition
Shuichiro Ogaki; Yu Shibata; Keiichi Noguchi; Ken Tanaka; Journal of Organic Chemistry 76 (2011) 1926–1929; doi:10.1021/jo1024255

data_4026127
_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
;
 Enantioselective Synthesis of Axially Chiral Hydroxy Carboxylic Acid
 Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1926
_journal_page_last               1929
_journal_paper_doi               10.1021/jo1024255
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H39 N O6 S, C H Cl3'
_chemical_formula_sum            'C43 H40 Cl3 N O6 S'
_chemical_formula_weight         805.17
_chemical_name_systematic
;
 (S,R)-(-)-4,6-Bis(2-methoxynaphthalen-1-yl)-7-methyl-2-
 (toluene-4-sulfonyl)-2,3-dihydro-1H-isoindole-5-
 carboxylic acid isopropyl 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             2010-12-7
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.0190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.2578(2)
_cell_length_b                   11.0728(2)
_cell_length_c                   14.0140(3)
_cell_measurement_reflns_used    31558
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.27
_cell_volume                     1986.99(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2009)'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS 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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35772
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    2.978
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.410
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881.  3088 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.007(14)
_refine_ls_extinction_coef       0.0036(2)
_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   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         6908
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.4977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                5299
_reflns_number_total             6908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1024255_si_003.cif
_cod_data_source_block           I
_cod_database_code               4026127