Syntheses of chiral lactones via asymmetric allylboration

M. Venkat Ram Reddy, Herbert C. Brown, P. Veeraraghavan Ramachandran

Research output: Contribution to journalArticlepeer-review

Abstract

The syntheses of lactenones and lactones of different ring sizes in high enantiomeric excesses involving asymmetric allylboration with B-allyldiisopinocampheylborane have been described (1). γ-Substituted γ-butyolactones have been synthesized from homoallyl alcohols via a protection-hydroboration-oxidation-deprotection-cyclization sequence. The unique nature of α-perfluoroalkyl homoallyl alcohols has been exploited for the synthesis of γ-perfluoroalkyl γ-butyrolactones without protecting the alcohols. Allylboration of formyl esters provide a general route to prepare ω-allyl and ω-propyllactones. The ring-closing metathesis of homoallyl enoates provides a methodology to prepare a variety of α-pyranone-containing natural products.

Original languageEnglish (US)
Pages (from-to)220-234
Number of pages15
JournalACS Symposium Series
Volume783
StatePublished - Dec 1 2001

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