Phosphine-Catalyzed Dual Umpolung Domino Michael Reaction: Facile Synthesis of Hydroindole- and Hydrobenzofuran-2-Carboxylates
Kishi, Kenta; Takizawa, Shinobu; Sasai, Hiroaki; ACS Catalysis 8 (2018) 5228–; doi:10.1021/acscatal.8b01011

data_4515637
_publ_section_title
;
 Phosphine-Catalyzed Dual Umpolung Domino Michael Reaction: Facile
 Synthesis of Hydroindole- and Hydrobenzofuran-2-Carboxylates
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5228
_journal_paper_doi               10.1021/acscatal.8b01011
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C13 H17 N O5 S'
_chemical_formula_sum            'C13 H17 N O5 S'
_chemical_formula_weight         299.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.357(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.923(4)
_cell_length_b                   16.864(9)
_cell_length_c                   14.255(8)
_cell_measurement_reflns_used    4432
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.11
_cell_volume                     1422.7(15)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11128
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         3.105
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632.00
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0615P)^2^+0.2423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2691
_reflns_number_total             3242
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs8b01011_si_002.cif
_cod_data_source_block           20170725_kishi
_cod_original_cell_volume        1422.7(14)
_cod_database_code               4515637
_shelx_res_checksum              69765
_shelx_hkl_checksum              77704