Efficient chirality transfer in the SmI2-mediated cyclization of aldehydo beta-alkoxyvinyl sulfoxides: asymmetric synthesis of 3-hydroxyoxanes.
Jung, Jae Hoon; Kim, Yong Wook; Kim, Min Ah; Choi, Soo Young; Chung, Young Keun; Kim, Tae-Rae; Shin, Seokmin; Lee, Eun; Organic letters 9 (2007) 3225–3228; doi:10.1021/ol071176+

data_1516663
_publ_section_title
;
 Efficient chirality transfer in the SmI2-mediated cyclization of aldehydo
 beta-alkoxyvinyl sulfoxides: asymmetric synthesis of 3-hydroxyoxanes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3225
_journal_page_last               3228
_journal_paper_doi               10.1021/ol071176+
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C13 H16 O3 S'
_chemical_formula_weight         252.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.095(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0338(17)
_cell_length_b                   5.4918(4)
_cell_length_c                   16.9616(18)
_cell_measurement_reflns_used    2224
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1329.6(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP32
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6750
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9430
_exptl_absorpt_correction_T_min  0.9237
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'R. H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.189
_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   0.17(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0608P)^2^+0.1022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                2845
_reflns_number_total             4965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol071176%2B%2B-file002.cif
_cod_data_source_block           jjh01
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1516663