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A novel stereoselective route to γ-butyrolactones

✍ Scribed by Mike Casey; Ajith C. Manage; Patrick J. Murphy

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
280 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

carbonyl compounds with sofr rlectrophiles restdted in intramolectdar aYsplacement of the stt@nyl group by the wrbonyl to give ~butyrolactones. This novel cyclisation wrks best for bznzylic svlfaridcs and provides a concise route to ttans-#J~ttbstitttted lactones with high stereoselectivity.

Conjugate additions of sulfoxides to c@-unsaturated esters proceed cleanly, with high stereoselectivity at the newly created chiral centres.u We now report that the resulting adducts can be transformed directly and stereoselectively into ~butyrolactones, using a novel displacement reaction of the sulfinyl group.

0

x LDA. THF. -78 Bu' ' c R%JH=CHC@,R'

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A new asymmetric route to synthetically
A new asymmetric route to synthetically useful γ-substituted γ-butyrolactones
✍ Jarosław Kiegiel; Jacek Nowacki; Aldona Tarnowska; Małgorzata Stachurska; Janusz 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 100 KB

The results of asymmetric hydrogenation of diethyl 3,4-dioxohexanedioate are presented. (R,R)-1,5-Dioxa-2,6-dioxobicyclo[3.3.0]octane, the product of hydrogenation and subsequent cyclization, was obtained in high enantiomeric excess. This compound was transformed into synthetically useful (R)-4-hydr