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Concomitant formation of chiral and racemic crystals of a diaryl sulfide

✍ Scribed by Lennartson, Anders; Wiklund, Tove; Håkansson, Mikael

Book ID
120358943
Publisher
Royal Society of Chemistry
Year
2007
Tongue
English
Weight
901 KB
Volume
9
Category
Article
ISSN
1466-8033

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Diastereoselective rhodium(II)-catalyzed
Diastereoselective rhodium(II)-catalyzed sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic allylic sulfides
✍ Andrew G.H Wee; Qing Shi; Zhongyi Wang; Kimberly Hatton 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 240 KB

The tandem sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic secondary allylic sulfides, (E)-9 and (Z)-10, is found to proceed with high diastereocontrol. The C-5 stereocenter bearing the sulfide group is essential for high diastereoselectivity in the reaction.