Catalytic Enantioselective Meerwein-Eschenmoser Claisen Rearrangement: Asymmetric Synthesis of Allyl Oxindoles
Elizabeth C. Linton; Marisa C. Kozlowski; Journal of the American Chemical Society 130 (2008) 16162–16163; doi:10.1021/ja807026z

data_4108770
_publ_section_title
;
 Catalytic Enantioselective Meerwein-Eschenmoser Claisen Rearrangement:
 Asymmetric Synthesis of Allyl Oxindoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16162
_journal_page_last               16163
_journal_paper_doi               10.1021/ja807026z
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C23 H27 N O6 S'
_chemical_formula_weight         445.52
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.954(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7058(10)
_cell_length_b                   13.9305(16)
_cell_length_c                   9.1612(10)
_cell_measurement_temperature    143(1)
_cell_volume                     1106.9(2)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7710
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8211
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.181
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.2669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                3275
_reflns_number_total             3619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807026z_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4108770