A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B- allyldiisopinocampheylborane

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

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

Asymmetric allylboration of aldehydes containing an adjacent ester group with B-allyldiisopinocampheylborane, followed by hydrolysis and cyclization, provides the corresponding allyl substituted lactones in high yields and ≥92% enantiomeric excess. Hydrogenation of these lactones provides the corresponding propyl substituted lactones without any loss of optical purity.

Original languageEnglish (US)
Pages (from-to)11-15
Number of pages5
JournalTetrahedron Asymmetry
Volume10
Issue number1
DOIs
StatePublished - Jan 15 1999
Externally publishedYes

Fingerprint Dive into the research topics of 'A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B- allyldiisopinocampheylborane'. Together they form a unique fingerprint.

  • Cite this