Enantioselective Baeyer-Villiger Oxidation: Desymmetrization of Meso Cyclic Ketones and Kinetic Resolution of Racemic 2-Arylcyclohexanones
Lin Zhou; Xiaohua Liu; Jie Ji; Yuheng Zhang; Xiaolei Hu; Lili Lin; Xiaoming Feng; Journal of the American Chemical Society 134 (2012) 17023–17026; doi:10.1021/ja309262f

data_4118786
_publ_contact_author_name
;
;
_publ_section_title
;
 Enantioselective Baeyer-Villiger Oxidation: Desymmetrization of Meso
 Cyclic Ketones and Kinetic Resolution of Racemic 2-Arylcyclohexanones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17023
_journal_page_last               17026
_journal_paper_doi               10.1021/ja309262f
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H13 Br O2'
_chemical_formula_sum            'C12 H13 Br O2'
_chemical_formula_weight         269.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
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_cell_measurement_reflns_used    640
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
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_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
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SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
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SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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_diffrn_ambient_temperature      293.15
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
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  1 omega   -4.00   90.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       20.0174   37.0000   60.0000 94

  2 omega    0.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       20.0174   37.0000  -30.0000 86

  3 omega   36.00   62.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       20.0174  -99.0000  -90.0000 26

  4 omega  -90.00  -59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.8924    0.0000   60.0000 31
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_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0360555000
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_diffrn_orient_matrix_UB_13      -0.0357444000
_diffrn_orient_matrix_UB_21      -0.0152792000
_diffrn_orient_matrix_UB_22      -0.0050365000
_diffrn_orient_matrix_UB_23      0.0517331000
_diffrn_orient_matrix_UB_31      0.0004648000
_diffrn_orient_matrix_UB_32      0.1297114000
_diffrn_orient_matrix_UB_33      0.0030698000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
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_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2648
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_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
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_exptl_absorpt_coefficient_mu    3.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76679
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
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empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         1921
_refine_ls_number_restraints     1
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_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0251P)^2^+0.1252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                1500
_reflns_number_total             1921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja309262f_si_002.cif
_cod_data_source_block           120817_s3_zl
_cod_original_cell_volume        1138.16(19)
_cod_database_code               4118786
_chemical_oxdiff_formula         C12H16O2Br1
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32