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Efficient Synthesis of Enantiomerically Pure α‐Ionone from ( R )‐ and ( S )‐α‐Damascone
Author(s) -
Fehr Charles,
Guntern Olivier
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750405
Subject(s) - ionone , chemistry , racemization , transposition (logic) , enone , yield (engineering) , stereochemistry , terpene , artificial intelligence , materials science , computer science , metallurgy
( R )‐ and ( S )‐α‐ionone (( R )‐ and ( S )‐ 1 , resp.) were prepared from ( R )‐ and ( S )‐α‐damascone (( R )‐ and ( S )‐ 3 , resp.) without racemization in 48% yield employing a new enone transposition. The described transposition is complementary to existing methods whose application is often prohibited by the structural requirements of the substrate. The now easily accessible α‐ionones of desired absolute configuration are useful as chiral building blocks for terpenoid synthesis.