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_4026935
_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            'C26 H26 N2 O7'
_chemical_formula_weight         478.49
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_audit_conform_dict_name         cif_core.dic
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_audit_creation_date             2008-08-29T11:40:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.826(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3130(3)
_cell_length_b                   6.2890(2)
_cell_length_c                   17.3747(6)
_cell_measurement_reflns_used    4112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.1878
_cell_measurement_theta_min      2.8741
_cell_volume                     1234.66(7)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
        (compiled Apr 21 2008,18:23:10)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
        (compiled Apr 21 2008,18:23:10)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
        (compiled Apr 21 2008,18:23:10)
;
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.356
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'ccd Xcalibur S'
_diffrn_measurement_method       '\w- amd \f-scans'
_diffrn_orient_matrix_UB_11      -0.0310772596
_diffrn_orient_matrix_UB_12      -0.0066395677
_diffrn_orient_matrix_UB_13      0.0343516537
_diffrn_orient_matrix_UB_21      -0.0525071216
_diffrn_orient_matrix_UB_22      0.0344235532
_diffrn_orient_matrix_UB_23      -0.0202925738
_diffrn_orient_matrix_UB_31      -0.0149263284
_diffrn_orient_matrix_UB_32      -0.107167114
_diffrn_orient_matrix_UB_33      -0.0086435446
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
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_diffrn_reflns_number            14493
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.97032
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_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
        (compiled Apr 21 2008,18:23:10)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       'small needles'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.088
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0202P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0544
_reflns_number_gt                2685
_reflns_number_total             4883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202330b_si_002_1.cif
_cod_data_source_block           x0584fin
_cod_database_code               4026935