l-Proline-Catalyzed Three-Component Domino [3+2+1] Annulation for the Regio- and Diastereoselective Synthesis of Highly Substituted Thienothiopyrans Containing Three or Four Stereocenters
Sethuraman Indumathi; Subbu Perumal; J. Carlos Menéndez; Journal of Organic Chemistry 75 (2010) 472–475; doi:10.1021/jo9021327

data_4025163
_publ_contact_author_address
;
Department of Physics
Thiagarajar College
Madurai - 625 009
India
;
_publ_contact_author_email       vasan692000@yahoo.co.in
_publ_contact_author_fax         '91 452 2312375'
_publ_contact_author_name        'Dr.N. Srinivasan'
_publ_contact_author_phone       '91 452 2311875'
_publ_section_title
;
 l-Proline-Catalyzed Three-Component Domino [3+2+1] Annulation for the
 Regio- and Diastereoselective Synthesis of Highly Substituted
 Thienothiopyrans Containing Three or Four Stereocenters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              472
_journal_page_last               475
_journal_paper_doi               10.1021/jo9021327
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C26 H27 Cl O6 S2'
_chemical_formula_sum            'C26 H27 Cl O6 S2'
_chemical_formula_weight         535.08
_chemical_name_systematic
;
Diethyl 7-(4-chlorophenyl)-2-(4-methylphenyl)-5,5-dioxo-2,3,4,5,6,7-
hexahydro-5-thieno[3,2-c]thiopyran-4,6-dicarboxylate
;
_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                 113.100(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0572(5)
_cell_length_b                   15.4093(6)
_cell_length_c                   15.1911(6)
_cell_measurement_reflns_used    1087
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.3
_cell_measurement_theta_min      4.5
_cell_volume                     2596.10(18)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLUTON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER AXS (Kappa APEX2 CCD Diffractometer)'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29752
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0911P)^2^+1.2958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1752
_reflns_number_gt                3932
_reflns_number_total             5932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9021327_si_002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025163