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_4107459
_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         'C15 H13 Br1 O4'
_chemical_formula_sum            'C15 H13 Br O4'
_chemical_formula_weight         337.17
_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             07-08-17
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 107.703(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4903(7)
_cell_length_b                   10.5136(7)
_cell_length_c                   12.9337(8)
_cell_measurement_reflns_used    4353
_cell_measurement_temperature    120
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     1358.92(16)
_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 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker KappaCCD ApexII'
_diffrn_measurement_device_type  Area
_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  0.089
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21386
_diffrn_reflns_theta_full        27.447
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_min         2.038
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.035
_exptl_absorpt_correction_T_max  0.70
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.10
_refine_diff_density_min         -1.19
_refine_ls_abs_structure_details 'Flack (1983), 2691 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.061(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0657
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         6204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000546
_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: 
 22.0 24.1 8.36 2.08 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0852
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0852
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4787
_reflns_number_total             6221
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.77
_oxford_diffrn_Wilson_scale      3.34
_oxford_refine_ls_r_factor_ref   0.0557
_oxford_refine_ls_scale          0.5732(6)
_oxford_reflns_number_all        6204
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'RPS_I_47_L_0m in P2(1)'
_cod_data_source_file            ja078251w-file003.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C15 H13 Br1 O4'
_cod_database_code               4107459