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_4110937
_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_absolute_configuration unk
_chemical_formula_moiety         'C19 H23 N O'
_chemical_formula_sum            'C19 H23 N O'
_chemical_formula_weight         281.38
_chemical_name_systematic
; 
 N-(2-tert-Butylphenyl)-N-phenylpropanamide 
;
_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_date             2006-05-18
_audit_creation_method           'maXus and SHELXL97 '
_cell_angle_alpha                90.00
_cell_angle_beta                 98.887(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1490(3)
_cell_length_b                   16.9310(12)
_cell_length_c                   13.2000(9)
_cell_measurement_reflns_used    3390
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.87
_cell_volume                     1578.54(17)
_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 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device       IP
_diffrn_measurement_method       ' phi scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3390
_diffrn_reflns_theta_full        27.06
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.4(15)
_refine_ls_extinction_coef       0.042(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   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0652P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                2649
_reflns_number_total             3390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja064026nsi20060608_033515.cif
_cod_data_source_block           6a
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4110937