Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols.
Yeh, Ming-Chang P; Liang, Chia-Jung; Liu, Cheng-Yuan; Shih, Ya-Fon; Lee, I-Chen; Liu, Hsiang-Fang; Wang, Jeng-Long; Organic & biomolecular chemistry 11 (2013) 3393–3399; doi:10.1039/c3ob27352k

data_7152866
_publ_section_title
;
 Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by
 one-pot epoxidation/spirocyclization of C(3)-functionalized
 cyclohex-2-en-1-ols.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3393
_journal_page_last               3399
_journal_paper_doi               10.1039/c3ob27352k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C11 H18 O4'
_chemical_formula_sum            'C11 H18 O4'
_chemical_formula_weight         214.25
_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                 112.4030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.1080(3)
_cell_length_b                   9.3204(2)
_cell_length_c                   16.7632(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2182.32(8)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13226
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.814
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0715P)^2^+1.2125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                3220
_reflns_number_total             3820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob27352k.txt
_cod_data_source_block           a14175
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152866