Amino Acid Mediated Intramolecular Asymmetric Aldol Reaction to Construct a New Chiral Bicyclic Enedione Containing a Seven-Membered Ring: Remarkable Inversion of Enantioselectivity Compared to the Six-Membered Ring
Takashi Nagamine; Kohei Inomata; Yasuyuki Endo; Leo A. Paquette; Journal of Organic Chemistry 72 (2007) 123–131; doi:10.1021/jo061824n

data_4022615
_publ_section_title
;
 Amino Acid Mediated Intramolecular Asymmetric Aldol Reaction
 to Construct a New Chiral Bicyclic Enedione Containing a Seven-Membered
 Ring: Remarkable Inversion of Enantioselectivity Compared
 to the Six-Membered Ring
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              123
_journal_page_last               131
_journal_paper_doi               10.1021/jo061824n
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H27 F3 O4'
_chemical_formula_sum            'C23 H27 F3 O4'
_chemical_formula_weight         424.45
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7640(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8455(8)
_cell_length_b                   12.1404(11)
_cell_length_c                   10.2121(9)
_cell_measurement_reflns_used    3905
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.35
_cell_volume                     1073.62(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6578
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_correction_T_min  0.9492
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0358P)^2^+0.1588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                2511
_reflns_number_total             2627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061824nsi20060904_125509.cif
_cod_data_source_block           D-220S-MTPAester
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022615