Enantioselective direct intermolecular aldol reactions with enantiotopic group selectivity and dynamic kinetic resolution.
Ward, Dale E.; Jheengut, Vishal; Akinnusi, Olukayode T.; Organic letters 7 (2005) 1181–1184; doi:10.1021/ol050195l

data_1506538
_publ_section_title
;
 Enantioselective direct intermolecular aldol reactions with enantiotopic
 group selectivity and dynamic kinetic resolution.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1181
_journal_page_last               1184
_journal_paper_doi               10.1021/ol050195l
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C14 H20 O5 S2'
_chemical_formula_sum            'C14 H20 O5 S2'
_chemical_formula_weight         332.42
_chemical_name_common            'compound 14'
_chemical_name_systematic
; 
(3S)-Tetahydro-3-[(1R,2R,4R,5S)-2-hydroxyl-spiro[3-oxa-7-thiabicyclo[3.3.1]nonane-9,2'-[1,3]dioxolane]-4-yl]-4H-thiopyran-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.9970(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3040(2)
_cell_length_b                   8.8750(3)
_cell_length_c                   20.5620(7)
_cell_measurement_reflns_used    3430
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1514.46(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Xtal3.7(Hall et al., 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'maXus(Mackay et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6378
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0577P)^2^+1.2752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1374
_reflns_number_gt                2504
_reflns_number_total             3472
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol050195lsi20050204_092119.cif
_cod_data_source_block           Ward-etal-14
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1506538