Synthesis of Octahydroquinolines through the Lewis Acid Catalyzed Reaction of Vinyl Allenes and Imines
David Regás; María M. Afonso; Matías L. Rodríguez; J. Antonio Palenzuela; Journal of Organic Chemistry 68 (2003) 7845–7852; doi:10.1021/jo034480z

data_4022476
_publ_section_title
;
 Synthesis of Octahydroquinolines through the Lewis Acid
 Catalyzed Reaction of Vinyl Allenes and Imines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7845
_journal_page_last               7852
_journal_paper_doi               10.1021/jo034480z
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C26 H31 N'
_chemical_formula_weight         357.52
_chemical_name_systematic
; 
 1-Benzyl-3-isopropylidene-4-methyl-2-phenyl-
1,2,3,5,6,7,8,8a-octahydroquinoline 
;
_space_group_IT_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.553(1)
_cell_length_b                   9.066(1)
_cell_length_c                   31.076(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2127.9(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2973
_diffrn_reflns_theta_full        28.60
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.150
_refine_ls_shift/su_mean         0.031
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.2853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2673
_reflns_number_total             2973
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            jo034480zsi20030813_074541.cif
_cod_data_source_block           togno1
_cod_database_code               4022476