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_7123840
_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         'C18 H18 O2 S'
_chemical_formula_sum            'C18 H18 O2 S'
_chemical_formula_weight         298.38
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-05 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                108.45(3)
_cell_angle_beta                 102.39(3)
_cell_angle_gamma                112.79(4)
_cell_formula_units_Z            1
_cell_length_a                   6.790(3)
_cell_length_b                   8.390(2)
_cell_length_c                   8.689(3)
_cell_measurement_reflns_used    4783
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      5.81
_cell_volume                     399.4(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7576
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.652
_diffrn_reflns_theta_min         6.385
_exptl_absorpt_coefficient_mu    1.805
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             158
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1101 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.081(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0436P)^2^+0.0257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2595
_reflns_number_total             2841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04758a2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7123840
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.737
_shelx_estimated_absorpt_t_max   0.774
_shelx_res_checksum              36664