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Development of new methods for asymmetric synthesis based on sulfoximines

✍ Scribed by Hans-Joachim Gais


Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
278 KB
Volume
18
Category
Article
ISSN
1042-7163

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✦ Synopsis


Abstract

Sulfoximine‐substituted bis(allyl)titanium complexes, which are configurationally labile at the Cα‐atoms, have emerged as valuable reagents in asymmetric synthesis. Their highly selective reactions with aldehydes and N‐sulfonyl imino esters allow the attainment of enantio‐ and diastereomerically pure sulfoximine‐substituted homoallylic alcohols and homoallylic amines, respectively, which are valuable starting materials for the asymmetric synthesis of homopropargylic alcohols, 2,3‐dihydrofurans, medium‐sized carbocycles and lactones, unsaturated mono‐ and bicyclic prolines, β‐amino acids, and vinyl oxiranes, respectively. The high synthetic versatility of the sulfoximine group stems from its ability to function as a chiral carbanion‐stabilizing nucleofuge. © 2007 Wiley Periodicals, Inc. 18:472–481, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20331


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Asymmetric Synthesis of Isocarbacyclin B
✍ Jörg Bund; Hans-Joachim Gais; Elmar Schmitz; Irene Erdelmeier; Gerhard Raabe 📂 Article 📅 1998 🏛 John Wiley and Sons 🌐 English ⚖ 575 KB

An asymmetric synthesis of isocarbacyclin (2) was achieved (97% ee), whose conversion to 8 has been already described, was isolated in 90% yield. The key step in the sequence from ketone 7 by the olefination-isomerization-coupling process with chiral sulfoximines. The vinylic sulfoximine 6 leading t