Desymmetrizing reductive aldol cyclizations of enethioate derivatives of 1,3-diones catalyzed by a chiral copper hydride.
Ou, Jun; Wong, Wing-Tak; Chiu, Pauline; Organic & biomolecular chemistry 10 (2012) 5971–5978; doi:10.1039/c2ob25206f

data_7152476
_publ_section_title
;
 Desymmetrizing reductive aldol cyclizations of enethioate derivatives of
 1,3-diones catalyzed by a chiral copper hydride.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5971
_journal_page_last               5978
_journal_paper_doi               10.1039/c2ob25206f
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H22 O3 S'
_chemical_formula_sum            'C15 H22 O3 S'
_chemical_formula_weight         282.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 91.746(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8058(3)
_cell_length_b                   8.7130(4)
_cell_length_c                   13.1696(5)
_cell_measurement_reflns_used    7329
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.80
_cell_volume                     780.58(6)
_computing_cell_refinement       'SAINT v7.34A (Bruker AXS Inc, 2007)'
_computing_data_collection       'APEX (Bruker AXS Inc, 2007)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2006)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex CCD'
_diffrn_measurement_method       \w
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7329
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack (1983). 1908 Friedel pairs'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.0373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1852
_reflns_number_gt                1908
_reflns_number_total             2515
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2ob25206f.txt
_cod_data_source_block           PC-O2-123-1_2-shelxl
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7152476