Organic Stereochemistry. Part 21. Issue 2 (18th February 2013)

• Record Type: Journal Article
• Authors: Testa, Bernard
• Is Part Of: Helvetica chimica acta. Volume 96:Issue 2(2013:Feb.)
• Page Start: 159
• Page End: 188
• Publication Date: 2013-02-18
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201200470
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>This review continues a general presentation of the principles of stereochemistry with special reference to medicinal compounds. Here, we explore stereoisomeric compounds characterized by a single or several stereogenic centers (often also called centers of chirality). The main focus will be on chiral tetrahedral structures, namely <italic>a</italic>) tetracoordinate centers, and <italic>b</italic>) tricoordinate centers where an electron lone pair plays the role of the fourth substituent, forming a tetrahedron. Following an overview of the main tetrahedral structures of interest in biological and medicinal stereochemistry, the review places emphasis on explaining the two dominant conventions, namely the <sc>d, l</sc><italic>‐</italic> and (<italic>R</italic>, <italic>S</italic>)‐convention, the latter being known as the <italic>CIP</italic> (<italic>CahnIngoldPrelog</italic>) convention. The review ends with a discussion of reactions of stereoisomerization at stereogenic C‐centers and its relevance to drug research.</p> </abstract>