Catalytic Enantioselective Vinylogous Mukaiyama-Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters
Xavier Jusseau; Pascal Retailleau; Laurent Chabaud; Catherine Guillou; Journal of Organic Chemistry 78 (2013) 2289–2300; doi:10.1021/jo3020648

data_4028012
_publ_contact_author_address
;Centre de Recherche de Gif
Institut de Chimie des Substances Naturelles
CNRS-UPR2301
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       catherine.guillou@icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_name        'Catherine Guillou'
_publ_contact_author_phone       +33169823075
_publ_section_title
;
 Catalytic Enantioselective Vinylogous Mukaiyama-Michael Addition of
 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2289
_journal_page_last               2300
_journal_paper_doi               10.1021/jo3020648
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C29 H25 O8 P'
_chemical_formula_sum            'C29 H25 O8 P'
_chemical_formula_weight         532.46
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.128(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.725(5)
_cell_length_b                   8.406(4)
_cell_length_c                   23.918(6)
_cell_measurement_reflns_used    5867
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      6.7
_cell_volume                     2548.2(17)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11821
_diffrn_reflns_theta_full        63.96
_diffrn_reflns_theta_max         63.96
_diffrn_reflns_theta_min         6.67
_exptl_absorpt_coefficient_mu    1.403
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       needle
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.00083(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+4.1153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                2175
_reflns_number_total             4157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3020648_si_004.cif
_cod_data_source_block           186
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028012