EnantioselectiveAldol Reaction Between Isatins and Cyclohexanone Catalyzed by Amino Acid Sulphonamides. Issue 4 (17th February 2015)

• Record Type: Journal Article
• Authors: Wang, Jun; Liu, Qi; Hao, Qing; Sun, Yanhua; Luo, Yiming; Yang, Hua
• Is Part Of: Chirality. Volume 27:Issue 4(2015)
• Page Start: 314
• Page End: 319
• Publication Date: 2015-02-17
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22433
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>Sulphonamides derived from primary <italic>α</italic>‐amino acid were successfully applied to catalyze the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">aldol reaction</named-content> between isatin and cyclohexanone under neat conditions. More interestingly, <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">molecular sieves</named-content>, as privileged additives, were found to play a vital role in achieving high <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselectivity</named-content>. Consequently, high yields (up to 99%) along with good <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselectivities</named-content> (up to 92% <italic>ee</italic>) and diastereoselectivities (up to 95:5 <italic>dr</italic>) were obtained. In addition, this reaction was also conveniently scaled up, demonstrating the applicability of this protocol. <italic>Chirality 27:314‐319, 2015</italic>. © 2015 Wiley Periodicals, Inc.</p> </abstract>