Ruthenium-catalysed synthesis of chiral exocyclic allylic alcohols via chemoselective transfer hydrogenation of 2-arylidene cycloalkanones?

Green Chemistry Pub Date: 2021-01-28 DOI: 10.1039/D1GC00026H

Abstract

An exclusive asymmetric reduction of C[double bond, length as m-dash]O bonds of 2-arylidene four-, five-, six-, and seven-membered cycloalkanones has been studied systematically. The asymmetric transfer hydrogenation was performed using a robust and commercially available chiral diamine-derived ruthenium complex as a catalyst and HCOOH/Et3N as a hydrogen source under mild conditions, giving 51 examples of chiral exocyclic allylic alcohols in up to 96% yield and 99% ee. This method was also applicable to the gram-scale synthesis of the active intermediates of the anti-inflammatory loxoprofen and natural product (?)-goniomitine.

Graphical abstract: Ruthenium-catalysed synthesis of chiral exocyclic allylic alcohols via chemoselective transfer hydrogenation of 2-arylidene cycloalkanones
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