Enantioselective Synthesis of α,α-Disubstituted Cyclopentenes by an N-Heterocyclic Carbene-Catalyzed Desymmetrization of 1,3-Diketones
Manabu Wadamoto; Eric M. Phillips; Troy E. Reynolds; Karl A. Scheidt; Journal of the American Chemical Society 129 (2007) 10098–10099; doi:10.1021/ja073987e

data_4109801
_publ_section_title
;
 Enantioselective Synthesis of \a,\a-Disubstituted Cyclopentenes by an
 N-Heterocyclic Carbene-Catalyzed Desymmetrization of 1,3-Diketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10098
_journal_page_last               10099
_journal_paper_doi               10.1021/ja073987e
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C16 H10 N O2'
_chemical_formula_weight         248.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.927(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.101(6)
_cell_length_b                   7.937(4)
_cell_length_c                   14.958(8)
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      2.27
_cell_measurement_theta_min      27.75
_cell_volume                     1317.8(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.1836
_diffrn_reflns_av_sigmaI/netI    0.1457
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10907
_diffrn_reflns_theta_full        28.82
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0826
_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^)+(0.0874P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1955
_reflns_number_gt                1803
_reflns_number_total             3164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja073987esi20070601_042516.cif
_cod_data_source_block           s24um
_cod_original_cell_volume        1317.8(13)
_cod_database_code               4109801