Synthesis of α-Cyclopropyl-β-homoprolines
Franca M. Cordero; Maria Salvati; Carolina Vurchio; Armin de Meijere; Alberto Brandi; Journal of Organic Chemistry 74 (2009) 4225–4231; doi:10.1021/jo9004684

data_4024566
_publ_contact_author_address
;
University of Florence
Department  of Organic Chemistry ?Ugo Schiff? and HeteroBioLab
Via della Lastruccia 13
50019 Sesto Fiorentino (FI)
Italy 
;
_publ_contact_author_email       franca.cordero@unifi.it
_publ_contact_author_name        'Prof.ssa Franca Cordero'
_publ_section_title
;
Synthesis of \a-Cyclopropyl-\b-homoprolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4225
_journal_page_last               4231
_journal_paper_doi               10.1021/jo9004684
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C13 H16 F3 N O5'
_chemical_formula_weight         323.27
_chemical_melting_point          390
_chemical_name_systematic
;
1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(trifluoroacetyl)tetrahydro-3aH-
[1,3]dioxolo[4,5-c]pyrrol-4-yl]cyclopropanecarboxylic Acid
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Tue Feb 24 11:50:53 2009'
;
_audit_creation_method
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0340(10)
_cell_length_b                   25.6730(10)
_cell_length_c                   8.0660(10)
_cell_measurement_reflns_used    1394
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7669
_cell_measurement_theta_min      5.1676
_cell_volume                     1456.6(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    Ortep3
_computing_publication_material  Encifer
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir2004
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Xcalibur CuK\a (Oxford Diffraction)'
_diffrn_measurement_method       'profile data from omega scan'
_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     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3494
_diffrn_reflns_theta_full        72.94
_diffrn_reflns_theta_max         72.94
_diffrn_reflns_theta_min         5.48
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 300
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  0.9085
_exptl_absorpt_correction_T_min  0.8353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'Diethyl ether and petroleum ether'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.177
_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   -0.3(3)
_refine_ls_extinction_coef       0.0180(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   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0683P)^2^+0.8724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                1604
_reflns_number_total             2147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9004684_si_003.cif
_cod_data_source_block           compound16
_cod_database_code               4024566