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_1504756
_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_formula_sum            'C43 H37 F3 N O4 P'
_chemical_formula_weight         719.71
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7407(2)
_cell_length_b                   15.7646(2)
_cell_length_c                   17.2946(2)
_cell_measurement_reflns_used    7371
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.2267
_cell_measurement_theta_min      3.7958
_cell_volume                     3746.30(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_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 0.992
_diffrn_orient_matrix_UB_11      -0.044780394
_diffrn_orient_matrix_UB_12      -0.0554966634
_diffrn_orient_matrix_UB_13      0.064251665
_diffrn_orient_matrix_UB_21      -0.0022193853
_diffrn_orient_matrix_UB_22      -0.076351079
_diffrn_orient_matrix_UB_23      -0.0557063526
_diffrn_orient_matrix_UB_31      0.1029825747
_diffrn_orient_matrix_UB_32      -0.0257203879
_diffrn_orient_matrix_UB_33      0.0267086624
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16150
_diffrn_reflns_theta_max         64.23
_diffrn_reflns_theta_min         3.79
_exptl_absorpt_coefficient_mu    1.137
_exptl_absorpt_correction_T_max  0.824
_exptl_absorpt_correction_T_min  0.688
_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    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.081
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                5401
_reflns_number_total             6112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801027p-file006.cif
_cod_data_source_block           (1S,2R)-11_ME
_cod_database_code               1504756