A highly regioselective hydroformylation of an α-chiral olefin to produce a versatile trifunctionalised orthogonally protected C5 synthon

This paper describes a highly regioselective hydroformylation of (R)-N-phthalimido-vinylglycinol, [(R)-PVG]. By judicious choice of the reaction conditions, catalyst-controlled preferential formation of the linear regioisomer could be achieved in excellent yield. The hydroformylation product cyclised to a hemi-acetal, which is an orthogonally protected trifunctionalised enantio-enriched C5 synthon. The value of this versatile intermediate was demonstrated by the ready formation of enantio-enriched amino-diols, diamino-alcohols and differentially protected (R)-3-aminopiperidine.

Graphical abstractA highly regioselective hydroformylation of (R)-N-phthalimido-vinylglycinol and the synthetic utility of the product is described.Download full-size image