Highly Enantioselective Synthesis of Atropisomeric Anilide Derivatives through Catalytic Asymmetric N-Arylation: Conformational Analysis and Application to Asymmetric Enolate Chemistry
Osamu Kitagawa; Masatoshi Yoshikawa; Hajime Tanabe; Tomofumi Morita; Masashi Takahashi; Yasuo Dobashi; Takeo Taguchi; Journal of the American Chemical Society 128 (2006) 12923–12931; doi:10.1021/ja064026n

data_4110936
_publ_contact_author_address
;
School of Pharmacy, Tokyo University of Pharmacy and Life Science,
Horinouchi Hachioji, Tokyo, 192-0392, Japan
;
_publ_contact_author_email       '  kitagawa@ps.toyaku.ac.jp '
_publ_contact_author_name        ' Osamu Kitagawa  '
_publ_section_title
;
 Highly Enantioselective Synthesis of Atropisomeric Anilide Derivatives
 through Catalytic Asymmetric N-Arylation: Conformational Analysis and
 Application to Asymmetric Enolate Chemistry
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12923
_journal_page_last               12931
_journal_paper_doi               10.1021/ja064026n
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C19 H22 N2 O3'
_chemical_formula_sum            'C19 H22 N2 O3'
_chemical_formula_weight         326.39
_chemical_name_systematic
; 
 N-(2-tert-Butylphenyl)-N-(4-nitrophenyl)propanamide 
;
_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_date             2006-05-18
_audit_creation_method           'maXus and SHELXL97 '
_cell_angle_alpha                95.477(2)
_cell_angle_beta                 91.773(2)
_cell_angle_gamma                94.758(3)
_cell_formula_units_Z            4
_cell_length_a                   8.4270(4)
_cell_length_b                   12.1600(5)
_cell_length_c                   16.8370(7)
_cell_measurement_reflns_used    7050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.76
_cell_volume                     1710.22(13)
_computing_cell_refinement
;        
DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_data_collection
;
DIP2000 software Xpress (MAC Science, 1989)
;
_computing_data_reduction
;
DIP2000 software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_molecular_graphics    'Platon     (A.L.Spek  2004)'
_computing_publication_material  'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et al, 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device       IP
_diffrn_measurement_method       ' phi scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7050
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_correction_T_min  0.9663
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0804P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                5530
_reflns_number_total             7050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja064026nsi20060608_033441.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4110936