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_4026126
_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         'C32 H33 N O5 S'
_chemical_formula_sum            'C32 H33 N O5 S'
_chemical_formula_weight         543.65
_chemical_name_systematic
;
  (R)-6-(2-Methoxynaphthalen-1-yl)-4,7-dimethyl-2-(toluene-4-
  sulfonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid 
  isopropyl ester
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-10-10
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.428(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6662(4)
_cell_length_b                   10.1239(3)
_cell_length_c                   19.1996(5)
_cell_measurement_reflns_used    18316
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.6
_cell_volume                     2848.18(14)
_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
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25214
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         4.61
_exptl_absorpt_coefficient_mu    1.343
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.663
_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    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 2274 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.00179(17)
_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   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5029
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0769P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                3677
_reflns_number_total             5029
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1024255_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        2848.19(14)
_cod_database_code               4026126