Asymmetric Formal trans-Dihydroxylation and trans-Aminohydroxylation of α,β-Unsaturated Aldehydes via an Organocatalytic Reaction Cascade
Łukasz Albrecht; Hao Jiang; Gustav Dickmeiss; Björn Gschwend; Signe Grann Hansen; Karl Anker Jørgensen; Journal of the American Chemical Society 132 (2010) 9188–9196; doi:10.1021/ja103538s

data_4102631
_publ_contact_author_address
;
Department of Chemistry
Aarhus University
Langelandsgade 140
DK-8000 Aarhus C
;
_publ_contact_author_email       jacobo@chem.au.dk
_publ_contact_author_fax         '+45 8619 6199'
_publ_contact_author_name        'Overgaard, Jacob'
_publ_contact_author_phone       '+45 8942 3891'
_publ_section_title
;
 Asymmetric Formal trans-Dihydroxylation and trans-Aminohydroxylation of
 \a,\b-Unsaturated Aldehydes via an Organocatalytic Reaction Cascade
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9188
_journal_page_last               9196
_journal_paper_doi               10.1021/ja103538s
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H24 N O7 S, C12 H24 N'
_chemical_formula_sum            'C34 H48 N2 O7 S'
_chemical_formula_weight         628.8
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-04-07T12:37:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.3720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1494(2)
_cell_length_b                   14.1915(3)
_cell_length_c                   24.3721(6)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.444
_cell_measurement_wavelength     0.71073
_cell_volume                     3473.03(13)
_computing_cell_refinement       'Saint+ v7.68A (Bruker-Nonius, 2010)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2010)'
_computing_data_reduction        'Saint+ v7.68A (Bruker-Nonius, 2010)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 12.00
_diffrn_detector_type            'APEX2 charged-coupled device'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method
;
            Narrow slices collected using \f- and \w-scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            56392
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         0.84
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.14
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 6774 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(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     799
_refine_ls_number_reflns         14168
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.4190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.133
_refine_ls_wR_factor_ref         0.1422
_reflns_Friedel_coverage         0.916
_reflns_number_gt                11953
_reflns_number_total             14168
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja103538s_si_002.cif
_cod_data_source_block           240310_mads_0m
_cod_database_code               4102631