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

Reaction of the sodium anion of (S)-N-(α-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. [ABSTRACT FROM AUTHOR]