An Experimental and in Situ IR Spectroscopic Study of the Lithiation-Substitution of N-Boc-2-phenylpyrrolidine and -piperidine: Controlling the Formation of Quaternary Stereocenters
Nadeem S. Sheikh; Daniele Leonori; Graeme Barker; James D. Firth; Kevin R. Campos; Anthony J. H. M. Meijer; Peter O'Brien; Iain Coldham; Journal of the American Chemical Society 134 (2012) 5300–5308; doi:10.1021/ja211398b

data_4117703
_publ_section_title
;
 An Experimental and in Situ IR Spectroscopic Study of the
 Lithiation-Substitution of N-Boc-2-phenylpyrrolidine and -piperidine:
 Controlling the Formation of Quaternary Stereocenters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5300
_journal_page_last               5308
_journal_paper_doi               10.1021/ja211398b
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H25 N O2'
_chemical_formula_sum            'C17 H25 N O2'
_chemical_formula_weight         275.38
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2746(7)
_cell_length_b                   11.2697(13)
_cell_length_c                   21.763(3)
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      19.06
_cell_measurement_theta_min      3.62
_cell_volume                     1538.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_sigmaI/netI    0.0760
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14173
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.221
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.175(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   1.259
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.259
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0643
_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^)+(0.0827P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1828
_reflns_number_gt                1380
_reflns_number_total             2063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211398b_si_001.cif
_cod_data_source_block           oic230_0m
_cod_database_code               4117703