Highly diastereo- and enantioselective organocatalytic addition of acetone to β-substituted α-ketoesters via dynamic kinetic resolution
Yang, Jin; Wang, Ting; Ding, Zhenhua; Shen, Zongxuan; Zhang, Yawen; Organic & Biomolecular Chemistry 7 (2009) 2208–2213; doi:10.1039/b822127h

data_7150624
_publ_section_title
;
 Highly diastereo- and enantioselective organocatalytic addition of
 acetone to \b-substituted \a-ketoesters via dynamic kinetic resolution
;
_journal_issue                   10
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2208
_journal_page_last               2213
_journal_paper_doi               10.1039/b822127h
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 Br O5'
_chemical_formula_sum            'C16 H19 Br O5'
_chemical_formula_weight         371.22
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6480(19)
_cell_length_b                   9.9528(19)
_cell_length_c                   17.941(3)
_cell_measurement_reflns_used    5460
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.1
_cell_volume                     1722.8(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16895
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    2.405
_exptl_absorpt_correction_T_max  0.485
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       0.0033(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0748
_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^)+(0.0549P)^2^+0.7152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                2208
_reflns_number_total             3146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822127h.txt
_cod_data_source_block           shelxl
_cod_database_code               7150624