A General Organocatalyzed Michael-Michael Cascade Reaction Generates Functionalized Cyclohexenes
Patrick G. McGarraugh; Joshua H. Jones; Stacey E. Brenner-Moyer; Journal of Organic Chemistry 76 (2011) 6309–6319; doi:10.1021/jo201140a

data_4026500
_publ_section_title
;
 A General Organocatalyzed Michael-Michael Cascade Reaction Generates
 Functionalized Cyclohexenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6309
_journal_page_last               6319
_journal_paper_doi               10.1021/jo201140a
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Br2 O4 C22 H20'
_chemical_formula_sum            'C22 H20 Br2 O4'
_chemical_formula_weight         508.21
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.0950(9)
_cell_length_b                   12.6448(14)
_cell_length_c                   20.093(3)
_cell_measurement_reflns_used    11656
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      3.15
_cell_volume                     2056.7(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD (SCX mini)'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14377
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.978
_exptl_absorpt_correction_T_max  0.672
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_description       block
_exptl_crystal_F_000             1016.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.350
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2003 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.008(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4679
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                2835
_reflns_number_total             4679
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo201140a_si_002.cif
_cod_data_source_block           '_jj01'
_cod_original_formula_sum        'Br2 O4 C22 H20'
_cod_database_code               4026500