Catalytic Enantioselective Alkylation of Sulfenate Anions to Chiral Heterocyclic Sulfoxides Using Halogenated Pentanidium Salts1. Issue 44 (10th September 2014)

• Record Type: Journal Article
• Authors: Zong, Lili; Ban, Xu; Kee, Choon Wee; Tan, Choon‐Hong
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 44(2014)
• Page Start: 11849
• Page End: 11853
• Publication Date: 2014-09-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201407512
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We report halogenated pentanidiums as phase‐transfer catalysts for the asymmetric alkylation of sulfenate anions to various sulfoxides with high enantioselectivities (up to 99 % <italic>ee</italic>) and yields (up to 99 %). This approach gives access to enantioenriched heterocyclic sulfoxides that might not be compatible with strong oxidants or organometallic reagents. Computational studies have revealed that the multiple noncovalent interactions such as halogen bonds and nonclassical hydrogen bonds are involved.</p> </abstract>