Synthesis of Isoquinuclidines from Highly Substituted Dihydropyridines via the Diels-Alder Reaction.
Martin, Rhia M.; Bergman, Robert G.; Ellman, Jonathan A.; Organic letters 15 (2013) 444–447; doi:10.1021/ol303040r

data_1508843
_publ_section_title
;
 Synthesis of Isoquinuclidines from Highly Substituted Dihydropyridines
 via the Diels-Alder Reaction.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              444
_journal_page_last               447
_journal_paper_doi               10.1021/ol303040r
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_sum            'C22 H31 N O2'
_chemical_formula_weight         341.48
_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                 99.420(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.6187(2)
_cell_length_b                   15.2421(3)
_cell_length_c                   8.3982(6)
_cell_measurement_reflns_used    11243
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      2.9
_cell_volume                     962.09(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11258
_diffrn_reflns_theta_full        68.32
_diffrn_reflns_theta_max         68.32
_diffrn_reflns_theta_min         5.89
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_correction_T_min  0.8458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.42(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0196P)^2^+0.2528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0642
_reflns_number_gt                3136
_reflns_number_total             3185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303040r_si_001.cif
_cod_data_source_block           12079
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1508843