Dispiroketals in synthesis (part 10): Further reactions of dispoke protected lactate and glycolate enolates

Geert Jan Boons*, Robert Downham, Kun Soo Kim, Steven V. Ley, Martin Woods

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

α-Hydroxy acids have been reacted with bis-dihydropyrans to give dispiroketal adducts (1,8,13,16-tetraoxadispiro[5.0.5.4]-hexadecan-14-ones). The enolates derived from these compounds undergo reaction with electrophiles with generally high levels of diastereoselectivity. Subsequent deprotection of these compounds gives α-hydroxy esters of high enantiomeric excess.

Original languageEnglish
Pages (from-to)7157-7176
Number of pages20
JournalTetrahedron
Volume50
Issue number24
DOIs
Publication statusPublished - 1 Jan 1994
Externally publishedYes

Funding

Acknowledgements We thank the SERC (MW, RD). KOSEF (KSK) and the Ron~soy Menlorial Fund (G-JB) for financial support. We also gratefully acknowledge the B.P. endowment (to SVL) ut Cambridge.

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