213532-97-9Relevant academic research and scientific papers
Practical asymmetric synthesis of both enantiomers of 6-(hydroxymethyl)piperidin-2-one
Hodgkinson, Timothy J.,Shipman, Michael
, p. 1141 - 1144 (2007/10/03)
A practical asymmetric synthesis of both enantiomers of 6 (hydroxymethyl)piperidin-2-one 1 is described. Asymmetric dihydroxylation (AD) of alkenyl ester 2 using the (DHQ)2AQN ligand provides diol (5S)-3 in ≤95% ee after recrystallisation. This diol can subsequently be transformed into (6R)-1 using a five step reaction sequence. By employing (DHQD)2AQN [1,4-bis(dihydroquininyl)anthraquinone] in the initial AD reaction, (6S)-1 can be prepared in an analogous fashion.
