Enantioselective Diels-Alder Reaction of Simple α,β-Unsaturated Ketones with a Cinchona Alkaloid Catalyst
Ravi P. Singh; Keith Bartelson; Yi Wang; Heng Su; Xiaojie Lu; Li Deng; Journal of the American Chemical Society 130 (2008) 2422–2423; doi:10.1021/ja078251w

data_4107460
_publ_section_title
;
 Enantioselective Diels-Alder Reaction of Simple \a,\b-Unsaturated Ketones
 with a Cinchona Alkaloid Catalyst
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2422
_journal_page_last               2423
_journal_paper_doi               10.1021/ja078251w
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H32 Br2 Cl2 O10'
_chemical_formula_sum            'C34 H32 Br2 Cl2 O10'
_chemical_formula_weight         831.34
_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
_audit_creation_date             07-07-12
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 95.895(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2732(9)
_cell_length_b                   10.6002(7)
_cell_length_c                   13.1907(9)
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    120
_cell_measurement_theta_max      19
_cell_measurement_theta_min      2
_cell_volume                     1707.0(2)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'KappaCCD ApexII'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.051
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10197
_diffrn_reflns_theta_full        18.446
_diffrn_reflns_theta_max         21.959
_diffrn_reflns_theta_min         1.552
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.588
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       fragment
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.79
_refine_ls_abs_structure_details 'Flack (1983), 1787 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.041(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.8504
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000401
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 18.3 18.3 5.26 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0907
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0907
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2738
_reflns_number_total             3981
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.3598(3)
_oxford_structure_analysis_title 'RPS_I_79_CHIR_L_0m in P2(1)'
_cod_data_source_file            ja078251w-file004.cif
_cod_data_source_block           RPS_I_79_chir_L_cif
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4107460