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_1506539
_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_absolute_configuration rmad
_chemical_formula_moiety         'C14 H24 O5 S2, H2 O'
_chemical_formula_sum            'C14 H26 O6 S2'
_chemical_formula_weight         354.47
_chemical_melting_point          164.0(10)
_chemical_name_common            'compound 15'
_chemical_name_systematic
; 
(3R,4S)-3-{(R)-Hydroxy-[(6S,10R)-10-hydroxymethyl-
1,4-dioxa-8-thiaspiro[4.5]dec-6-yl]methyl}-
tetrahydro-2H-thiopyran-4-ol
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 95.915(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5560(8)
_cell_length_b                   5.3200(3)
_cell_length_c                   15.0250(7)
_cell_measurement_reflns_used    1894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1634.35(14)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.042
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3442
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.08
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.266
_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   0.00(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0000P)^2^+1.5009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                3006
_reflns_number_total             3442
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol050195lsi20050204_092151.cif
_cod_data_source_block           Ward-etal-15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '163-165' was changed to '164.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1506539