Dearomatising cyclisation of lithiated 1-naphthamides with a phenylglycinol-derived chiral auxiliary: Asymmetric synthesis of an arylkainoid and a kainoid-like pyroglutamate

Ryan A. Bragg, Jonathan Clayden*, Michael Bladon, Osamu Ichihara

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

46 Citations (Scopus)

Abstract

1-Naphthamides of N-benzylphenylglycinols undergo a diastereoselective dearomatising cyclisation on treatment with t-BuLi and DMPU or HMPA. A new pyrrolidinone ring is formed bearing three new stereogenic centers of defined absolute stereochemistry. Removal of the phenylglycinol auxiliary gives enantiomerically pure substituted lactams exhibiting the stereochemistry of the kainoids. These may be converted to kainoid-like pyroglutamates, or alternatively, using the method of the previous paper, to analogues of acromelic acid.

Original languageEnglish
Pages (from-to)3411-3414
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number20
Early online date25 Apr 2001
DOIs
Publication statusPublished - 14 May 2001

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