Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels-Alder Reaction
Marko Weimar; Gerd Dürner; Jan W. Bats; Michael W. Göbel; Journal of Organic Chemistry 75 (2010) 2718–2721; doi:10.1021/jo100053j

data_4025353
_publ_section_title
;
 Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen
 Bond-Promoted Diels-Alder Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2718
_journal_page_last               2721
_journal_paper_doi               10.1021/jo100053j
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H38 O3 Si'
_chemical_formula_sum            'C35 H38 O3 Si'
_chemical_formula_weight         534.74
_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                 94.74(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.822(3)
_cell_length_b                   8.970(4)
_cell_length_c                   17.061(5)
_cell_measurement_reflns_used    60
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     1498.0(9)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  SIEMENS_SMART_CCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19160
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         221
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thin_plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          1.2
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(15)
_refine_ls_extinction_coef       0.0034(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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5481
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0520
_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^)+(0.05P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                3703
_reflns_number_total             5481
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo100053j_si_002.cif
_cod_data_source_block           ent-5
_cod_original_cell_volume        1497.9(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025353