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-(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.