Highly Enantioselective Quinoline Synthesis via Ene-type Cyclization of 1,7-Enynes Catalyzed by a Cationic BINAP-Palladium(II) Complex
Manabu Hatano; Koichi Mikami; Journal of the American Chemical Society 125 (2003) 4704–4705; doi:10.1021/ja0292748

data_4113667
_publ_section_title
;
 Highly Enantioselective Quinoline Synthesis via Ene-type Cyclization of
 1,7-Enynes Catalyzed by a Cationic BINAP-Palladium(II) Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4704
_journal_page_last               4705
_journal_paper_doi               10.1021/ja0292748
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C23 H23 N O4 S'
_chemical_formula_weight         409.48
_chemical_name_systematic
; 
manuscript number (JA0292748) 
[1-(Toluene-4-sulfonyl)-2,3-dihydro-1H-quinolin-4
-ylidene-3-spirocyclopent-2'-ene]-acetic acid
 methyl ester. 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.1700(10)
_cell_angle_beta                 90.207(3)
_cell_angle_gamma                72.859(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7403(2)
_cell_length_b                   14.6538(7)
_cell_length_c                   8.4165(3)
_cell_measurement_temperature    233(2)
_cell_volume                     1015.85(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.895
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4172
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.189
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             432
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.804
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.804
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0859P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.1862
_reflns_number_gt                3957
_reflns_number_total             4172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0292748si20030313_020403.cif
_cod_data_source_block           aaa
_cod_original_cell_volume        1015.85(6)
_cod_database_code               4113667