Phosphine-catalyzed domino reaction: highly stereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and allylic carbonates.
Xie, Peizhong; Huang, You; Chen, Ruyu; Organic letters 12 (2010) 3768–3771; doi:10.1021/ol101611v

data_1503171
_publ_section_title
;
 Phosphine-catalyzed domino reaction: highly stereoselective synthesis of
 trans-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and
 allylic carbonates.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3768
_journal_page_last               3771
_journal_paper_doi               10.1021/ol101611v
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C25 H23 Br N O3 P S'
_chemical_formula_sum            'C25 H23 Br N O3 P S'
_chemical_formula_weight         528.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 110.871(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2760(10)
_cell_length_b                   22.735(3)
_cell_length_c                   11.8940(15)
_cell_measurement_reflns_used    8978
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      1.80
_cell_volume                     2343.7(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD camera'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22426
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    1.939
_exptl_absorpt_correction_T_max  0.8297
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0424P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                4613
_reflns_number_total             5587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101611v_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               1503171