Asymmetric deprotonation-substitution of N-Pop-benzylamines using [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis of N-heterocycles.
Oña-Burgos, Pascual; Fernández, Ignacio; Roces, Laura; Torre-Fernández, Laura; García-Granda, Santiago; López-Ortiz, Fernando; Organic letters 10 (2008) 3195–3198; doi:10.1021/ol801027p

data_1504754
_publ_section_title
;
 Asymmetric deprotonation-substitution of N-Pop-benzylamines using
 [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis
 of N-heterocycles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3195
_journal_page_last               3198
_journal_paper_doi               10.1021/ol801027p
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H26 N1 O2 P1'
_chemical_formula_sum            'C27 H26 N O2 P'
_chemical_formula_weight         427.46
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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
_cell_angle_alpha                100.869(3)
_cell_angle_beta                 103.617(3)
_cell_angle_gamma                90.203(3)
_cell_formula_units_Z            2
_cell_length_a                   9.9856(4)
_cell_length_b                   10.1967(4)
_cell_length_c                   11.5731(5)
_cell_measurement_reflns_used    5913
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.16
_cell_measurement_theta_min      4.00
_cell_measurement_wavelength     1.54184
_cell_volume                     1123.29(8)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
Direct methods using SIR-92 (Altomare et al., 1993)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0827
_diffrn_measured_fraction_theta_max 0.94
_diffrn_orient_matrix_UB_11      0.00639433
_diffrn_orient_matrix_UB_12      0.1442042455
_diffrn_orient_matrix_UB_13      0.0713603795
_diffrn_orient_matrix_UB_21      0.1416871562
_diffrn_orient_matrix_UB_22      -0.0226399279
_diffrn_orient_matrix_UB_23      0.0794370867
_diffrn_orient_matrix_UB_31      0.0715524118
_diffrn_orient_matrix_UB_32      0.0484434996
_diffrn_orient_matrix_UB_33      -0.0896716899
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20071
_diffrn_reflns_theta_max         61.04
_diffrn_reflns_theta_min         4.01
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        XABS2
  Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
        Cubic fit to sin(theta)/lambda - 24 parameters
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.91
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         6098
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.91
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                4187
_reflns_number_total             6098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801027p-file004.cif
_cod_data_source_block           (1S,2R)-8
_cod_database_code               1504754