Journal
GREEN CHEMISTRY
Volume 23, Issue 4, Pages 1628-1632Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1gc00026h
Keywords
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Funding
- 111 Project [D20015, 2019SSPY158]
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The asymmetric reduction of C = O bonds of 2-arylidene cycloalkanones using a chiral ruthenium complex as a catalyst and HCOOH/Et3N as a hydrogen source resulted in high yields and high enantiomeric excess. This method is not only suitable for small-scale synthesis, but also applicable for the gram-scale synthesis of pharmaceutically important compounds.
An exclusive asymmetric reduction of C = 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.
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