A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates. Straightforward Syntheses of the Pheromones (+)-Vittatalactone and (+)-Norvittatalactone
Christian F. Weise; Matthias C. Pischl; Andreas Pfaltz; Christoph Schneider; Journal of Organic Chemistry 77 (2012) 1477–1488; doi:10.1021/jo202330b

data_4026936
_publ_contact_author
;
 Prof. Dr. Christoph Schneider

 Structure Determination:
 L\"onnecke, Peter
 Institut f\"ur Anorganische Chemie
 Universit\"at Leipzig
 Johannisallee 29
 04103 Leipzig
 Bundesrepublik Deutschland
;
_publ_contact_author_email       schneider@chemie.uni-leipzig.de
_publ_contact_author_fax         '49 / 341 / 9736599'
_publ_contact_author_phone       '49 / 341 / 9736559'
_publ_section_title
;
 A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates.
 Straightforward Syntheses of the Pheromones (+)-Vittatalactone and
 (+)-Norvittatalactone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1477
_journal_page_last               1488
_journal_paper_doi               10.1021/jo202330b
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_sum            'C24 H32 N2 O5'
_chemical_formula_weight         428.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_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      2.3
_audit_creation_date             2008-11-17T18:55:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0740(3)
_cell_length_b                   11.6141(3)
_cell_length_c                   21.7822(6)
_cell_measurement_reflns_used    2591
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      32.1196
_cell_measurement_theta_min      2.7994
_cell_volume                     2295.55(12)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
        (compiled Jan 10 2008,16:37:18)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
        (compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
        (compiled Jan 10 2008,16:37:18)
;
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX  (L.J. Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'ccd Xcalibur S'
_diffrn_measurement_method       '\w- amd \f-scans'
_diffrn_orient_matrix_UB_11      -0.016584266
_diffrn_orient_matrix_UB_12      0.0108708584
_diffrn_orient_matrix_UB_13      0.0312840829
_diffrn_orient_matrix_UB_21      -0.0043940194
_diffrn_orient_matrix_UB_22      -0.0600786518
_diffrn_orient_matrix_UB_23      0.0055380506
_diffrn_orient_matrix_UB_31      0.0762338735
_diffrn_orient_matrix_UB_32      -0.0010823855
_diffrn_orient_matrix_UB_33      0.0071250053
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.1584
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11320
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.24
_exptl_crystal_description       needles
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_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   0.0(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.672
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5680
_refine_ls_number_restraints     211
_refine_ls_restrained_S_all      0.666
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0545
_reflns_number_gt                2728
_reflns_number_total             5680
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202330b_si_002_2.cif
_cod_data_source_block           x0638fin
_cod_database_code               4026936