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Asymmetric wittig reaction of chiral arsonium ylides—I. Asymmetric olefination of 4-substituted cyclohexanones

✍ Scribed by Wei-Min Dai; Jinlong Wu; Xian Huang

Book ID
104361239
Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
236 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis

Asymmetric Wittig-type olefination of 4-substituted cyclohexanones with chiral ligand-modified stable arsonium ylides has been examined. The 8-phenylmentholderived chiral arsonium ylide of 4 reacted with prochiral ketones 9a-d at -15°C to give the 4-substituted cyclohexylideneacetates lla--d in 58-69% yield and in up to 80% diastereomeric excess (de). (~) 1997 Elsevier Science Ltd

📜 SIMILAR VOLUMES

Asymmetric Wittig reactions of chiral ar
Asymmetric Wittig reactions of chiral arsonium ylides. Part 2: Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides
✍ Wei-Min Dai; Chi Wai Lau 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 103 KB

Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides with chiral ligand-derived stable arsonium ylides proceeded in a kinetic resolution manner. The (E)-olefin products were obtained in excellent chemical yields and in up to 88:12 diastereoselectivity. Effects of the ami