Bifunctional phosphine-catalyzed domino reaction: highly stereoselective synthesis of cis-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and allenes.
Meng, Xiangtai; Huang, You; Chen, Ruyu; Organic letters 11 (2009) 137–140; doi:10.1021/ol802453c

data_1503729
_publ_section_title
;
 Bifunctional phosphine-catalyzed domino reaction: highly stereoselective
 synthesis of cis-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl
 imines and allenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              137
_journal_page_last               140
_journal_paper_doi               10.1021/ol802453c
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C20 H13 N3 O5 P S'
_chemical_formula_sum            'C26 H26 N O3 P S'
_chemical_formula_weight         463.51
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.580(9)
_cell_angle_beta                 79.743(13)
_cell_angle_gamma                89.960(13)
_cell_formula_units_Z            12
_cell_length_a                   15.176(6)
_cell_length_b                   22.472(9)
_cell_length_c                   22.477(8)
_cell_measurement_reflns_used    5556
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.0
_cell_volume                     7100(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1250
_diffrn_reflns_av_sigmaI/netI    0.3695
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43918
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9727
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2928
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1741
_refine_ls_number_reflns         24862
_refine_ls_number_restraints     2028
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.2833
_refine_ls_R_factor_gt           0.0710
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.2329
_reflns_number_gt                5284
_reflns_number_total             24862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802453c_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               1503729