Dynamic Kinetic Resolution of α-Keto Esters via Asymmetric Transfer Hydrogenation
Kimberly M. Steward; Emily C. Gentry; Jeffrey S. Johnson; Journal of the American Chemical Society 134 (2012) 7329–7332; doi:10.1021/ja3027136

data_4117897
_publ_contact_author_name
;
;
_publ_section_title
;
 Dynamic Kinetic Resolution of \a-Keto Esters via Asymmetric Transfer
 Hydrogenation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7329
_journal_page_last               7332
_journal_paper_doi               10.1021/ja3027136
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 Cl O6'
_chemical_formula_sum            'C15 H15 Cl O6'
_chemical_formula_weight         326.72
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-13
_audit_creation_method
;
  Olex2 1.2-alpha
  (compiled Jan 11 2012 18:49:03, GUI svn.r4030)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.943(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1401(5)
_cell_length_b                   8.7933(4)
_cell_length_c                   9.4025(4)
_cell_measurement_reflns_used    6747
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.63
_cell_measurement_theta_min      4.71
_cell_volume                     755.26(6)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
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.
;
_computing_publication_material
;
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.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100.
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7839
_diffrn_reflns_theta_full        66.70
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_min         4.71
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_T_max  0.8151
_exptl_absorpt_correction_T_min  0.5329
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0715 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.6538.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.042(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0386P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                2492
_reflns_number_total             2534
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3027136_si_001.cif
_cod_data_source_block           x1201010
_cod_database_code               4117897