Totally Selective Reaction of CO~2~ with Enantiopure Amino Epoxides under Mild Reaction Conditions. Synthesis and Synthetic Applications of Enantiopure (4R,1'S)- or (4S,1'S)-4-(1-Aminoalkyl)-2-oxo-1,3-dioxolanes
José M. Concellón; Virginia del Solar; Santiago García-Granda; M. Rosario Díaz; Journal of Organic Chemistry 72 (2007) 7567–7573; doi:10.1021/jo070829x

data_4024189
_publ_contact_author
;     Santiago Garc\'ia-Granda
      Departamento de Qu\'imica F\'isica y Anal\'itica
      Facultad de Qu\'imica
      Universidad de Oviedo
      Avda. Juli\'an Claver\'ia, 8
      33071 Oviedo
      Spain
;
_publ_contact_author_email       sgg@uniovi.es
_publ_contact_author_fax         '0034 98 5103125'
_publ_contact_author_phone       '0034 98 5103477'
_publ_section_title
;
 Totally Selective Reaction of CO~2~ with Enantiopure Amino
 Epoxides under Mild Reaction Conditions. Synthesis and Synthetic
 Applications of Enantiopure (4R,1'S)- or
 (4S,1'S)-4-(1-Aminoalkyl)-2-oxo-1,3-dioxolanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7567
_journal_page_last               7573
_journal_paper_doi               10.1021/jo070829x
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H25 N O3'
_chemical_formula_sum            'C25 H25 N O3'
_chemical_formula_weight         387.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 91.697(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0013(8)
_cell_length_b                   9.2305(6)
_cell_length_c                   21.6130(2)
_cell_measurement_reflns_used    4129
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.65
_cell_measurement_theta_min      0.00
_cell_volume                     2193.8(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.613
_diffrn_measured_fraction_theta_max 0.613
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.1002
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8285
_diffrn_reflns_theta_full        61.22
_diffrn_reflns_theta_max         61.22
_diffrn_reflns_theta_min         4.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0871P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1871
_reflns_number_gt                1724
_reflns_number_total             3094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070829x.cif
_cod_data_source_block           3c
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024189