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Synthesis of an Enantiomerically Pure Building Block for the Synthesis of Hydroporphyrins
Author(s) -
Etornam Adukpo Genevieve,
Borrmann Tobias,
Manski René,
Sáez Díaz Rosa I.,
Stohrer WolfDieter,
Montforts FranzPeter
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600656
Subject(s) - diastereomer , chemistry , pyrrolidine , enantiomer , lactam , lactone , alkylation , enantioselective synthesis , stereochemistry , optically active , block (permutation group theory) , yield (engineering) , organic chemistry , catalysis , materials science , geometry , mathematics , metallurgy
The enantiomerically pure pyrrolidine diester 4 i s a useful building block for the synthesis of chiral hydroporphyrin compounds. Treatment of optically active aromatic amines with bislactone 5 gave pairs of N ‐alkylated lactam‐lactone diastereomers 6 and 8 . These diastereomers were separated by MPL chromatography and in the case of 8 they could be debenzylated to yield the enantiomerically pure lactam‐lactone 7 and its enantiomer. The (–)‐lactam‐lactone enantiomer 7 was further transformed into building block 4 .(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)