Enantioselective Rh(I)-catalyzed cyclization of arylboron compounds onto ketones.
Low, Darryl W.; Pattison, Graham; Wieczysty, Martin D.; Churchill, Gwydion H.; Lam, Hon Wai; Organic letters 14 (2012) 2548–2551; doi:10.1021/ol300845q

data_1507684
_publ_section_title
;
 Enantioselective Rh(I)-catalyzed cyclization of arylboron compounds onto
 ketones.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2548
_journal_page_last               2551
_journal_paper_doi               10.1021/ol300845q
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H21 N O3 S'
_chemical_formula_sum            'C22 H21 N O3 S'
_chemical_formula_weight         379.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.9480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.08970(10)
_cell_length_b                   11.20050(10)
_cell_length_c                   18.59690(10)
_cell_measurement_reflns_used    41920
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.6288
_cell_measurement_theta_min      3.9435
_cell_volume                     1864.87(3)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            57059
_diffrn_reflns_theta_full        74.79
_diffrn_reflns_theta_max         74.79
_diffrn_reflns_theta_min         4.63
_exptl_absorpt_coefficient_mu    1.726
_exptl_absorpt_correction_T_max  0.8844
_exptl_absorpt_correction_T_min  0.7662
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 3572 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.009(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         7589
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.3162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                7513
_reflns_number_total             7589
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol300845q_si_003.cif
_cod_data_source_block           hl2003
_cod_depositor_comments
'Adding full bibliography for 1507683--1507684.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1507684