Organocatalytic Asymmetric Conjugate Addition to Allenic Esters and Ketones
Petteri Elsner; Luca Bernardi; Giorgio Dela Salla; Jacob Overgaard; Karl Anker Jørgensen; Journal of the American Chemical Society 130 (2008) 4897–4905; doi:10.1021/ja710689c

data_4107659
_publ_contact_author             'Overgaard, Jacob'
_publ_contact_author_email       jacobo@chem.au.dk
_publ_section_title
;
 Organocatalytic Asymmetric Conjugate Addition to Allenic Esters and
 Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4897
_journal_page_last               4905
_journal_paper_doi               10.1021/ja710689c
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H23 Cl1 O5'
_chemical_formula_sum            'C20 H23 Cl O5'
_chemical_formula_weight         378.83
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2007-07-05T09:21:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.276(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5352(3)
_cell_length_b                   6.8650(2)
_cell_length_c                   15.2561(5)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.584
_cell_measurement_theta_min      2.724
_cell_measurement_wavelength     0.71073
_cell_volume                     982.63(5)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.931
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31193
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         30.46
_diffrn_reflns_theta_min         2.17
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2004)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.28
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2250 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0329P)^2^+0.0959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.750
_reflns_number_gt                4664
_reflns_number_total             5250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710689c-file002.cif
_cod_data_source_block           07jo0030_01
_cod_database_code               4107659