Development of the Ireland-Claisen rearrangement of alkoxy- and aryloxy-substituted allyl glycinates

James P Tellam, David R Carbery

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The Ireland-Claisen rearrangement of 3-alkoxy- and 3-aryloxy-substituted allyl glycinates is presented. This [3,3]-sigmatropic rearrangement route offers direct access to syn -alkoxy and -aryloxy -amino acid systems. In particular, N,N-diboc glycine esters rearrange with excellent diastereoselectivities (dr 25:1). The synthesis of substrates, rearrangement optimization, and a discussion of stereoselection are presented.
Original languageEnglish
Pages (from-to)7809-7821
Number of pages13
JournalJournal of Organic Chemistry
Volume75
Issue number22
DOIs
Publication statusPublished - 19 Nov 2010

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