Stereoselective Total Synthesis of Aminoiminohexitols via Carbamate Annulation
Anna L. Win-Mason; Seino A. K. Jongkees; Stephen G. Withers; Peter C. Tyler; Mattie S. M. Timmer; Bridget L. Stocker; Journal of Organic Chemistry 76 (2011) 9611–9621; doi:10.1021/jo201151b

data_4026750
_publ_section_title
;
 Stereoselective Total Synthesis of Aminoiminohexitols via Carbamate
 Annulation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9611
_journal_page_last               9621
_journal_paper_doi               10.1021/jo201151b
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.14
_chemical_melting_point          472.1
_chemical_name_systematic
6,7-dibenzyloxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxaza-5-carbonitrile
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2011-06-01
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   6.9022(2)
_cell_length_b                   8.7137(3)
_cell_length_c                   30.7371(9)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      2.43
_cell_volume                     1848.64(10)
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_solution    'smtbx-flip (Bourhis, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996725
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            33420
_diffrn_reflns_theta_full        24.49
_diffrn_reflns_theta_max         24.49
_diffrn_reflns_theta_min         0.66
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6759
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 SADABS-2008/1 (Bruker,2008) was used for absorption correction.
 R(int) was 0.0634 before and 0.0514 after correction.
 The Ratio of minimum to maximum transmission is 0.907126560193.
 The \l/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.339559
_refine_diff_density_min         -0.301287
_refine_diff_density_rms         0.107520
_refine_ls_d_res_high            0.857423
_refine_ls_d_res_low             15.368550
_refine_ls_goodness_of_fit_ref   1.058932
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058932
_refine_ls_R_factor_all          0.042587
_refine_ls_R_factor_gt           0.035161
_refine_ls_shift/su_max          0.0019
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0799P)^2^+0.3043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.078790
_reflns_number_gt                2841
_reflns_number_total             3043
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            jo201151b_si_002.cif
_cod_data_source_block           ALWB
_cod_database_code               4026750