Chiral Phosphine Oxide-Sc(OTf)3 Complex Catalyzed Enantioselective Bromoaminocyclization of 2-Benzofuranylmethyl N-Tosylcarbamates. Approach to a Novel Class of Optically Active Spiro Compounds.
Li, Zequan; Shi, Yian; Organic letters 17 (2015) 5752–5755; doi:10.1021/acs.orglett.5b02817

data_1555410
_publ_section_title
;
 Chiral Phosphine Oxide-Sc(OTf)3 Complex Catalyzed Enantioselective
 Bromoaminocyclization of 2-Benzofuranylmethyl N-Tosylcarbamates. Approach
 to a Novel Class of Optically Active Spiro Compounds.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5752
_journal_page_last               5755
_journal_paper_doi               10.1021/acs.orglett.5b02817
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H14 N4 O5 S'
_chemical_formula_sum            'C17 H14 N4 O5 S'
_chemical_formula_weight         386.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.46(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3457(17)
_cell_length_b                   10.924(2)
_cell_length_c                   9.879(2)
_cell_measurement_reflns_used    2930
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4495
_cell_measurement_theta_min      1.8643
_cell_volume                     849.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.1006
	          2theta: -20.2863
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.1006
	          2theta: -20.2863
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.1006
	          2theta: -20.2863
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.1006
	          2theta: -20.2863
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0399
_diffrn_orient_matrix_UB_12      -0.0540
_diffrn_orient_matrix_UB_13      -0.1079
_diffrn_orient_matrix_UB_21      0.0410
_diffrn_orient_matrix_UB_22      0.0753
_diffrn_orient_matrix_UB_23      -0.0646
_diffrn_orient_matrix_UB_31      0.0827
_diffrn_orient_matrix_UB_32      -0.0132
_diffrn_orient_matrix_UB_33      0.0370
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14253
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.2255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3795
_reflns_number_total             3864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02817_si_006.cif
_cod_data_source_block           sa4217a
_cod_database_code               1555410
_shelxl_version_number           2013-4
_diffrn_number_total             3870
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              58767
_shelx_hkl_checksum              28026
_olex2_submission_special_instructions 'No special instructions were received'