Organocatalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-oxindoles via Morita-Baylis-Hillman Reaction
Yun-Lin Liu; Bo-Lun Wang; Jun-Jie Cao; Long Chen; Yong-Xue Zhang; Chao Wang; Jian Zhou; Journal of the American Chemical Society 132 (2010) 15176–15178; doi:10.1021/ja107858z

data_4103433
_publ_section_title
;
 Organocatalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-oxindoles
 via Morita-Baylis-Hillman Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15176
_journal_page_last               15178
_journal_paper_doi               10.1021/ja107858z
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H10 Cl N O3'
_chemical_formula_weight         251.66
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6773(3)
_cell_length_b                   7.5444(3)
_cell_length_c                   24.3301(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1225.66(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14147
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.8471
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+0.4318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                2047
_reflns_number_total             2134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja107858z_si_001.cif
_cod_data_source_block           z
_cod_database_code               4103433