Enantioselective Construction of a Polyhydroxylated Pyrrolidine Skeleton from 3-Vinylaziridine-2-carboxylates: Synthesis of (+)-DMDP and a Potential Common Intermediate for (+)-Hyacinthacine A1and (+)-1-epi-Australine
Yukari Kondo; Noriyuki Suzuki; Masato Takahashi; Takuya Kumamoto; Hyuma Masu; Tsutomu Ishikawa; Journal of Organic Chemistry 77 (2012) 7988–7999; doi:10.1021/jo301178b

data_4027507
_publ_section_title
;
 Enantioselective Construction of a Polyhydroxylated Pyrrolidine Skeleton
 from 3-Vinylaziridine-2-carboxylates: Synthesis of (+)-DMDP and a
 Potential Common Intermediate for (+)-Hyacinthacine A1and
 (+)-1-epi-Australine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7988
_journal_page_last               7999
_journal_paper_doi               10.1021/jo301178b
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_sum            'C13 H19 N O4'
_chemical_formula_weight         253.29
_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                 92.5870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6958(6)
_cell_length_b                   6.1371(4)
_cell_length_c                   10.4129(6)
_cell_measurement_reflns_used    1987
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.81
_cell_volume                     618.98(7)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3516
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.505
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2150
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.505
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0325P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                2081
_reflns_number_total             2150
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301178b_si_001.cif
_cod_data_source_block           a111219mas1
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4027507