Regio- and Stereoselective Cross-aldol Reactions via Dialkylboryl Triflates
- 1 January 1980
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 53 (1), 174-178
- https://doi.org/10.1246/bcsj.53.174
Abstract
New borylating reagents, (Bu2BOTf and 9-BBNOTf), were prepared in high yields. The triflates reacted with enolizable ketones in the presence of tertiary amines to generate selectively one of the regioisomers of vinyloxyboranes by the choice of the reagents (the dialkylboryl triflates and tertiary amines) under mild reaction conditions. Vinyloxyboranes thus generated showed remarkable reactivity toward aldehydes to give only one regioisomer of the corresponding cross-aldols in good yields. High stereoselectivity was also observed in these reactions.Keywords
This publication has 9 references indexed in Scilit:
- Titanium Tetrachloride in Organic Synthesis [New synthetic methods (21)]Angewandte Chemie-International Edition, 1977
- A new and highly effective aldol synthesisJournal of the American Chemical Society, 1977
- Fluoride ion catalyzed aldol reaction between enol silyl ethers and carbonyl compoundsJournal of the American Chemical Society, 1977
- Tetrahedron report number 25Tetrahedron, 1976
- A review of annulationTetrahedron, 1976
- Organoboranes and organoborate anions. New classes of electrophiles and nucleophiles in organic synthesisJournal of Chemical Education, 1975
- Reactions of Vinyloxyboranes. A Convenient Method for the Preparation of β-Hydroxy Thiolesters, Esters and KetonesBulletin of the Chemical Society of Japan, 1973
- Chemistry of carbanions. XXIII. Use of metal complexes to control the aldol condensationJournal of the American Chemical Society, 1973
- Chemistry of carbanions. XVIII. Preparation of trimethylsilyl enol ethersThe Journal of Organic Chemistry, 1969