Asymmetric allylboration of α,β-enals as a surrogate for the enantioselective synthesis of allylic amines and α-amino acids

P. Veeraraghavan Ramachandran, Thomas E. Burghardt, M. Venkat Ram Reddy

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

(Chemical Equation Presented) Optically pure allylic amines have been synthesized from α,β-unsaturated aldehydes via allylboration with (-)-B-allyldiisopinocampheylborane, followed by Overman rearrangement. By incorporating crotyl and alkoxyallylboration, functionalization at δ-position was readily accomplished. By applying this methodology, the synthesis of several chiral α-amino acids has been achieved.

Original languageEnglish (US)
Pages (from-to)2329-2331
Number of pages3
JournalJournal of Organic Chemistry
Volume70
Issue number6
DOIs
StatePublished - Mar 18 2005

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