Synthesis of 5-Fluoro- and 5-Hydroxymethanoprolines via Lithiation of N-BOC-methanopyrrolidines. Constrained Cγ-Exo and Cγ-Endo Flp and Hyp Conformer Mimics
Grant R. Krow; Matthew D. Shoulders; Ramakrishna Edupuganti; Deepa Gandla; Fang Yu; Philip E. Sonnet; Matthew Sender; Amit Choudhary; Charles DeBrosse; Charles W. Ross; Patrick Carroll; Ronald T. Raines; Journal of Organic Chemistry 77 (2012) 5331–5344; doi:10.1021/jo300700a

data_4027244
_publ_section_title
;
 Synthesis of 5-Fluoro- and 5-Hydroxymethanoprolines via Lithiation of
 N-BOC-methanopyrrolidines. Constrained C\g-Exo and C\g-Endo Flp and Hyp
 Conformer Mimics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5331
_journal_page_last               5344
_journal_paper_doi               10.1021/jo300700a
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C21 H30 F2 N2 O5'
_chemical_formula_weight         428.47
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      13
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.916(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.464(3)
_cell_length_b                   6.1223(9)
_cell_length_c                   19.024(3)
_cell_measurement_temperature    143(1)
_cell_volume                     2161.6(6)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11659
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3641
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.050
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       0.0034(12)
_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   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         11659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.1252
_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^)+(0.1277P)^2^+20.7022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3161
_refine_ls_wR_factor_ref         0.3533
_reflns_number_gt                8350
_reflns_number_total             11659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300700a_si_003.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2161.7(6)
_cod_original_sg_symbol_H-M      'P 2/c '
_cod_database_code               4027244