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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 5
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Original Articles

Asymmetric Cyanohydrin Synthesis Catalyzed by Mn(salen) Complex/Triphenylphosphine Oxide

Sung Soo Kim Department of Chemistry, Inha University, Incheon, South KoreaCorrespondence[email protected]
&
Sang Hyuck Lee Department of Chemistry, Inha University, Incheon, South Korea
Pages 751-759 | Received 15 Oct 2004, Published online: 20 Aug 2006
 
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Abstract

Various aldehydes undergo enantioselective silylcyanation with (CH3)3SiCN trimethylsilylcyanation (TMSCN) employing chiral Mn(salen) and achiral POPh3 as the catalysts. This is the double activation where Mn(salen) plays the role of Lewis acid and POPh3 Lewis base. Numerous aldehydes are subject to the enantioselective addition of TMSCN at 0°C. Hydrolysis of the adduct gave cyanohydrin with up to 96% yield and 62% ee.

Acknowledgment

The authors warmly thank the Inha University for the financial support in 2005.

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