The Vinylfluoro Group as an Acetonyl Cation Equivalent: Stereoselective Synthesis of 6-Substituted 4-Hydroxy Pipecolic Acid Derivatives
Nirupam Purkayastha; Deepak M. Shendage; Roland Fröhlich; Günter Haufe; Journal of Organic Chemistry 75 (2010) 222–225; doi:10.1021/jo901872a

data_4025124
_publ_section_title
;
 The Vinylfluoro Group as an Acetonyl Cation Equivalent: Stereoselective
 Synthesis of 6-Substituted 4-Hydroxy Pipecolic Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              222
_journal_page_last               225
_journal_paper_doi               10.1021/jo901872a
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C11 H22 N2 O2'
_chemical_formula_weight         214.31
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   'at N and O from difmap, others geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.489(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.5675(13)
_cell_length_b                   9.4469(5)
_cell_length_c                   12.9022(6)
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     2953.5(3)
_computing_cell_refinement       'Collect (Nonius B.v., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12291
_diffrn_reflns_theta_full        68.17
_diffrn_reflns_theta_max         68.17
_diffrn_reflns_theta_min         5.02
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.9247
_exptl_absorpt_correction_T_min  0.8159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.964
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_platon_squeeze_details
;
 ?
;
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0699
_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^)+(0.1320P)^2^+2.0831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2177
_reflns_number_gt                2272
_reflns_number_total             2639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901872a_si_002.cif
_cod_data_source_block           haf5006
_cod_database_code               4025124