A novel stereoselective synthesis of N-heterocycles by intramolecular hydrovinylation

Ulrich Bothe, H. C. Rudbeck, David Ackland Tanner, Mogens Johannsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A novel method for the synthesis of bicyclic amines has been developed. Cyclisation of 1,6-dienes by intramolecular hydrovinylation in the presence of catalytic amounts of allylpalladium chloride dimer afforded bicyclic amines in one step. Added phosphines, silver salts, as well as the nature of the N-protecting group influenced the yield and selectivity of the reactions. Most strikingly, intramolecular hydrovinylation allowed the preparation of diastereomerically pure bicyclic amines as e.g. hexahydroindoles 2a-2d.
Original languageEnglish
JournalRoyal Chemical Society. Journal. Perkin Transactions 1
Volume1
Issue number24
Pages (from-to)3305-3311
ISSN1472-7781
DOIs
Publication statusPublished - 2001

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