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Intramolecular Cycloaddition Reactions of ω‐Unsaturated Chiral Nitrones
Author(s) -
Marcus Jan,
Brussee Johannes,
van der Gen Arne
Publication year - 1998
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/(sici)1099-0690(199811)1998:11<2513::aid-ejoc2513>3.0.co;2-u
Subject(s) - cycloaddition , chemistry , intramolecular force , amine gas treating , ring (chemistry) , yield (engineering) , nitrone , enantiomeric excess , enantiomer , hydrogen cyanide , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , metallurgy
The intramolecular 1,3‐dipolar cycloaddition of ω‐un‐saturated chiral nitrones is described. Starting materials for this reaction are O ‐protected chiral cyanohydrins, prepared by an R‐oxynitrilase catalyzed asymmetric addition of hydrogen cyanide to ω‐unsaturated aldehydes. Intramolecular cycloaddition, followed by reductive opening of the isoxazolidine ring, produced five‐ and seven‐membered ring compounds with chiral hydroxy and amine functionalities of high enantiomeric purity in excellent yield.