A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres

M Koutsaplis, P C Andrews, S D Bull, P J Duggan, B H Fraser, P Jensen

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20 Citations (Scopus)

Abstract

Reaction of the sodium anion of (S)-N-(alpha-methylbenzyl)allylamine with two equivalents of tert-butyl cinnamate results in a remarkable tandem aza-allyl conjugate addition-Michael addition-ring closure reaction, resulting in a chiral aminocyclohexane containing six new vicinal stereogenic centres with excellent levels of stereocontrol.
Original languageEnglish
Pages (from-to)3580-3582
Number of pages3
JournalChemical Communications
Issue number34
DOIs
Publication statusPublished - 2007

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