Recent Progress in the Chemically Catalyzed Enantioselective Synthesis of Cyanohydrins

Abstract

The catalytic enantioselective cyanation of aldehydes and ketones has received growing attention because the resulting enantiomerically pure cyanohydrins are versatile building blocks for many biologically active compounds. To date, both metal-based and organic catalysts have been successfully developed to promote these reactions enantioselectively. Great advances have been made in the catalytic enan-

Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous–organic biphasic system

“…The reverse reaction, synthesis of optically active cyanohydrins, has attracted the attention of scientists and industry. Optically active cyanohydrins, containing hydroxyl and cyano groups attached to the same carbon atom, are versatile building blocks in the fine chemical and pharmaceutical industries (Brunel and Holmes, 2004;Holt and Hanefeld, 2009;Wang et al, 2010b).…”

Enantioselective synthesis of cyanohydrins catalysed by hydroxynitrile lyases – a review

“…[7][8][9]15,[20][21][22] Various reviews concentrate on all aspects of catalyst preparation, modification and mechanisms, including the enantioselectivity and its modification in HNLs; 4,6 similar reviews exist for chemical catalysts. 2,23,24 While HNL immobilisation for reaction engineering has recently been reviewed, 7 we herein introduce the asymmetric synthesis catalysed by HNLs and the essential background information for their successful application.…”

“…Final hydrolysis-induced lactonisation gave a 1 : 5 : 6 : 1 mixture of desired 3′-deoxyribolactone stereoisomers 20 in moderate yields. 41 Acetone cyanohydrin was used as a cyanide source for (R)-PaHNL in the chemo-enzymatic synthesis of D-and L-(2cyano-2-hydroxy/acetoxy)mannosides (23,24). This synthesis involves also lipase PS-D as the second enzyme for diastereomeric kinetic resolution by acylation.…”

Kongresse – Symposien – Seminare – Messen

“…in 2006 12. In addition, two reports dealing with the general field of enantioselective synthesis of cyanohydrins were independently published in 2008 by North and Khan,5b,c followed by a microreview published by Feng in 2010 7b. For the reader’s convenience, the review has been divided into three parts.…”