Asymmetric Multicomponent Domino Reactions and Highly Enantioselective Conjugated Addition of Thiols to α,β-Unsaturated Aldehydes
Mauro Marigo; Tobias Schulte; Johan Franzén; Karl Anker Jørgensen; Journal of the American Chemical Society 127 (2005) 15710–15711; doi:10.1021/ja055291w

data_4112067
_publ_contact_author_address
;
Department of Chemistry
University of Aarhus
Langelandsgade 140
DK-8000 Aarhus C
Denmark
;
_publ_contact_author_email       kaj@chem.au.dk
_publ_contact_author_fax         '+45 8619 6199'
_publ_contact_author_name        'J\/orgensen, K. A.'
_publ_contact_author_phone       '+45 8942 3333'
_publ_section_title
;
 Asymmetric Multicomponent Domino Reactions and Highly Enantioselective
 Conjugated Addition of Thiols to \a,\b-Unsaturated Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15710
_journal_page_last               15711
_journal_paper_doi               10.1021/ja055291w
_journal_volume                  127
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H20 O1 S1'
_chemical_formula_sum            'C13 H20 O S'
_chemical_formula_weight         224.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-06-23T10:34:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4034(1)
_cell_length_b                   8.6305(3)
_cell_length_c                   26.9086(8)
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      33.006
_cell_measurement_theta_min      2.478
_cell_measurement_wavelength     0.71073
_cell_volume                     1254.86(6)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2004)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2004)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2004)'
_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-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            45485
_diffrn_reflns_theta_full        33.16
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+0.2882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                4042
_reflns_number_total             4661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja055291wrom20050804_030513.cif
_cod_data_source_block           05jo0027_0m
_cod_database_code               4112067