Highly enantioselective construction of axial chirality by palladium-catalyzed cycloisomerization of N-alkenyl arylethynylamides.
Imase, Hidetomo; Suda, Takeshi; Shibata, Yu; Noguchi, Keiichi; Hirano, Masao; Tanaka, Ken; Organic letters 11 (2009) 1805–1808; doi:10.1021/ol900373z

data_1503857
_publ_section_title
;
 Highly enantioselective construction of axial chirality by
 palladium-catalyzed cycloisomerization of N-alkenyl arylethynylamides.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1805
_journal_page_last               1808
_journal_paper_doi               10.1021/ol900373z
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H28 Br N O2, C6 H6'
_chemical_formula_sum            'C31 H34 Br N O2'
_chemical_formula_weight         532.50
_chemical_name_systematic
;
 1-(2,2-Dimethylpropyl)-3-bromo-4-(2-methoxynaphthalen-1-yl)-
 5,6,7,8-tetrahydro-1H-quinolin-2-one
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.15783(17)
_cell_length_b                   17.0989(3)
_cell_length_c                   17.1807(3)
_cell_measurement_reflns_used    40344
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.6
_cell_volume                     2690.31(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47828
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    2.288
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 2127 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.024(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4918
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.7022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                4431
_reflns_number_total             4918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900373z_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        2690.30(8)
_cod_database_code               1503857