The first synthesis of both enantiomers of 2-Hydroxycyclobutanone (cas 17082-63-2) acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode☆

Add time:08/11/2019    Source:sciencedirect.com

A new practical enzymatic synthesis of (R)-(+)- and (S)-(−)-2-acetoxycyclobutanone acetals with 97–99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-Hydroxycyclobutanone (cas 17082-63-2) acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)-(−)-2-benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction.

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