An Experimental and Computational Study of Stereoselectivity and Reactivity in Lewis Acid Promoted Lithiation-Substitution of Tertiary Amines
Satinder V. Kessar; Paramjit Singh; Kamal Nain Singh; P. Venugopalan; Amarjit Kaur; Prasad V. Bharatam; Arvind K.Sharma; Journal of the American Chemical Society 129 (2007) 4506–4507; doi:10.1021/ja0675144

data_4109297
_publ_contact_author
;     'Prof. S.V.Kessar'
      Department of Chemistry
      Panjab University
      Chandigarh 160 014
      India
;
_publ_contact_author_email       svkessar@pu.ac.in
_publ_contact_author_fax         '091 172 2545074'
_publ_contact_author_phone       '091 172 2541435'
_publ_section_title
;
 An Experimental and Computational Study of Stereoselectivity and
 Reactivity in Lewis Acid Promoted Lithiation-Substitution of Tertiary
 Amines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4506
_journal_page_last               4507
_journal_paper_doi               10.1021/ja0675144
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C21 H25 N O'
_chemical_formula_weight         307.42
_chemical_melting_point          366
_chemical_name_systematic
;
(octahydro-indolizin-3-yl)-diphenyl-methanol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-08-25T10:50:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0430(10)
_cell_length_b                   8.2140(10)
_cell_length_c                   26.677(2)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.243
_cell_measurement_theta_min      10.355
_cell_volume                     1762.1(3)
_computing_cell_refinement       'XSCANS (Siemens)'
_computing_data_collection       'XSCANS (Siemens)'
_computing_data_reduction        'XSCANS (Siemens)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2990
_diffrn_reflns_theta_full        24
_diffrn_reflns_theta_max         24
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_preparation       'ethyl actate-hexanes (1:1, V/V)'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0163(14)
_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   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.3713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                2200
_reflns_number_total             2763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0675144si20061020_070023.cif
_cod_data_source_block           kamal4
_cod_database_code               4109297