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Chiral ketone-catalyzed asymmetric epoxidation of olefins with Oxone®

✍ Scribed by Koichiro Matsumoto; Kiyoshi Tomioka

Book ID
104232245
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
64 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Chiral ketones 1 and 2 bearing 1-aza-7-oxabicyclo[3.5.0]decane skeleton and their C 2 -symmetric analogue 3 were readily prepared and evaluated as a chiral dioxirane precursor for asymmetric epoxidation of olefins with Oxone ® . The ketone 2, bearing a diphenyl steric wall, was not effective and gave quite poor selectivity. Good selectivity up to 83% ee was obtained using 1 and 3, which suggested that Coulomb repulsion by carbonyl and ether oxygen atoms are operative as an electronic wall rather than a steric wall.

📜 SIMILAR VOLUMES

ChemInform Abstract: Chiral Ketone Catal
ChemInform Abstract: Chiral Ketone Catalyzed Asymmetric Epoxidation of Olefins
✍ Michael Frohn; Yian Shi 📂 Article 📅 2001 🏛 John Wiley and Sons ⚖ 24 KB 👁 1 views

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