Organocatalytic Enantioselective Desymmetrization of Cyclic Enones via Phosphine Promoted [3+2] Annulations
Nathalie Pinto; Pascal Retailleau; Arnaud Voituriez; Angela Marinetti; Chem.Commun. 47 (2011) 1015–; doi:10.1039/c0cc03164j

data_7105839
_publ_contact_author_address
;
Centre de Recherche de Gif
Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       angela.marinetti@icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_name        'Angela Marinetti'
_publ_contact_author_phone       +33169823036
_publ_section_title
;
 Organocatalytic Enantioselective Desymmetrization of Cyclic Enones via
 Phosphine Promoted [3+2] Annulations
;
_journal_coden_Cambridge         182
_journal_name_full               Chem.Commun.
_journal_page_first              1015
_journal_paper_doi               10.1039/c0cc03164j
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C27 H28 O3'
_chemical_formula_sum            'C27 H28 O3'
_chemical_formula_weight         400.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                89.178(2)
_cell_angle_beta                 81.131(8)
_cell_angle_gamma                89.707(5)
_cell_formula_units_Z            2
_cell_length_a                   6.273(3)
_cell_length_b                   10.862(4)
_cell_length_c                   16.439(4)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      0.998
_cell_volume                     1106.6(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18785
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'parallelepipedic block'
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.046(7)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0718P)^2^+0.2490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                2871
_reflns_number_total             4005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03164J.TXT
_cod_data_source_block           global
_cod_database_code               7105839