Lewis Base-Catalyzed Asymmetric Sulfenylation of Alkenes: Construction of Sulfenylated Lactones and Application to the Formal Syntheses of (-)-Nicotlactone B and (−)-Galbacin
Luo, Hui-Yun; Xie, Yu-Yang; Song, Xu-Feng; Dong, Jia-Wei; Zhu, Deng; Chen, Zhi-Min; Chemical Communications  (2019) –; doi:10.1039/C9CC04758A

data_7123839
_publ_section_title
;
 Lewis Base-Catalyzed Asymmetric Sulfenylation of Alkenes: Construction of
 Sulfenylated Lactones and Application to the Formal Syntheses of
 (-)-Nicotlactone B and (&#x2212;)-Galbacin
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04758A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 Br O2 S'
_chemical_formula_sum            'C16 H13 Br O2 S'
_chemical_formula_weight         349.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-02-27 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.29670(10)
_cell_length_b                   10.3438(2)
_cell_length_c                   28.0395(6)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      68.11
_cell_measurement_theta_min      3.15
_cell_volume                     1536.23(5)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20349
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.384
_diffrn_reflns_theta_min         3.152
_exptl_absorpt_coefficient_mu    4.902
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.5074
_refine_diff_density_max         0.972
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1155P)^2^+1.3770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2062
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2568
_reflns_number_total             2814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04758a2.cif
_cod_data_source_block           ta_a
_cod_database_code               7123839
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.412
_shelx_estimated_absorpt_t_max   0.441
_shelx_res_checksum              82246