Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.
Tao, Zhonglin; Robb, Kevin A.; Panger, Jesse L.; Denmark, Scott E.; Journal of the American Chemical Society 140 (2018) 15621–15625; doi:10.1021/jacs.8b10288

data_4133484
_publ_section_title
;
 Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of
 Alkenylboronates by 1,2-Boronate Migration.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15621
_journal_page_last               15625
_journal_paper_doi               10.1021/jacs.8b10288
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H37 B O2 S'
_chemical_formula_sum            'C30 H37 B O2 S'
_chemical_formula_weight         472.52
_chemical_name_systematic
2-((1S,2S)-1-(2,6-dimethylphenyl)-4-phenyl-2-(phenylthio)butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
_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_Int_Tables_number      19
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5200(2)
_cell_length_b                   13.4283(4)
_cell_length_c                   20.6016(6)
_cell_measurement_reflns_used    29296
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.36
_cell_volume                     2633.66(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            49437
_diffrn_reflns_theta_full        28.2994
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1291 before and 0.0565 after correction. The Ratio of minimum to maximum transmission is 0.9382. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1916
_exptl_crystal_description       block
_exptl_crystal_F_000             1016.8973
_exptl_crystal_recrystallization_method 'Hexane/Diethyl ether'
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.2864
_refine_diff_density_min         -0.1977
_refine_diff_density_rms         0.0418
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.00(5)
_refine_ls_d_res_high            0.7496
_refine_ls_d_res_low             8.6419
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0408
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     314
_refine_ls_number_reflns         6522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0408
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.8477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.997
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              27
_reflns_limit_l_min              -27
_reflns_number_gt                6203
_reflns_number_total             6522
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ja8b10288_si_002.cif
_cod_data_source_block           mo_DD48M_0m
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4133484
_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:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C26(H26a,H26b,H26c), C27(H27a,H27b,
 H27c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c)
;
_olex2_exptl_crystal_mounting_method
'The data crystal was mounted using Paratone oil to a 0.3 mm cryo-loop with the (-2,1,0) scattering planes roughyl normal to the spindle axis'
_olex2_submission_special_instructions 'No special instructions were received'