Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 30, Pages 4375-4378Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700708
Keywords
Gold; Chirality; Ene reaction; Heterocycles; Synthetic methods
Categories
Funding
- Japan Society for the Promotion of Science (JSPS) (KAKENHI) [JP16H00996]
- Grants-in-Aid for Scientific Research [16J02647, 16H00996] Funding Source: KAKEN
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Enantioenriched isoxazoles having a chiral side chain at the 4-position were efficiently synthesized by chirality transfer in a gold-catalyzed cyclization/intermolecular methylene-transfer sequence followed by a carbonyl ene reaction. The chiral information of the enantioenriched O-propargylic oximes was completely retained during the gold-catalyzed reaction. The subsequent carbonyl ene reaction between the resulting 4-methylenated isoxazoline and glyoxylates proceeded with excellent levels of chirality transfer by using BF3OEt2 as a Lewis acid. According to the relationship of absolute configuration between the starting propargylic oxime and the obtained alcohol having an isoxazole, the carbonyl ene reaction proceeded in an endo manner.
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