Stereoselective deconjugation of macrocyclic α,β-unsaturated esters by sequential amidation and olefin transposition: application to enantioselective phase-transfer catalysis.
Homberg, Alexandre; Hrdina, Radim; Vishe, Mahesh; Guénée, Laure; Lacour, Jérôme; Organic & biomolecular chemistry 17 (2019) 6905–6910; doi:10.1039/c9ob01355e

data_7156936
_publ_section_title
;
 Stereoselective deconjugation of macrocyclic \a,\b-unsaturated esters by
 sequential amidation and olefin transposition: application to
 enantioselective phase-transfer catalysis.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6905
_journal_page_last               6910
_journal_paper_doi               10.1039/c9ob01355e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C30 H38 N2 O8'
_chemical_formula_sum            'C30 H38 N2 O8'
_chemical_formula_weight         554.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-11
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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2019-06-14 deposited with the CCDC.    2019-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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  1 omega -124.00  -91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -18.00   40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -26.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -48.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega -119.00   -4.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   55.00   80.00   1.0000    2.0000
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  7 omega   58.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega    4.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  100.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  111.0000 -180.0000 77

 10 omega   75.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000 -150.0000 25

 11 omega  103.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  111.0000   90.0000 75

 12 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000 -120.0000 26

 13 omega  112.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000 -120.0000 64

 14 omega   78.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000  -30.0000 25

 15 omega   55.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  -30.0000  150.0000 32

 16 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000 -150.0000 26

 17 omega  124.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -60.0000 50

 18 omega   77.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000 -120.0000 30

 19 omega   77.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000  -60.0000 33

 20 omega  100.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999  111.0000   60.0000 59

 21 omega   78.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   61.0000  -90.0000 25

 22 omega  116.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -90.0000 55

 23 omega   74.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   30.0000    0.0000 32

 24 omega  135.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000 -150.0000 42

 25 omega   79.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   45.0000  -60.0000 26

 26 omega   80.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   45.0000  -30.0000 27

 27 omega   83.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   45.0000  -90.0000 29

 28 omega   74.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -30.0000 52

 29 omega  148.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -30.0000 26

 30 omega   79.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   45.0000 -120.0000 29

 31 omega   74.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -90.0000 27

 32 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   77.0000  -60.0000 26

 33 omega  131.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999   30.0000    0.0000 41

 34 omega   34.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.3999 -111.0000  -60.0000 51
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
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(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.3240P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01355e2.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 7156936--7156938.cif.'
_cod_original_cell_volume        1420.93(7)
_cod_database_code               7156936
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H38 N2 O8'
_reflns_odcompleteness_completeness 99.96
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_reflns_odcompleteness_theta     67.29
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              96321
_shelx_hkl_checksum              45475
_olex2_submission_special_instructions 'No special instructions were received'