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Asymmetric synthesis of α-methylene-γ-butyrolactones fused to carbocyclic rings via the Hosomi reaction of chiral allylsilanes.

✍ Scribed by Kiyoshi Nishitani; Koji Yamakawa

Book ID
104225411
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
263 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

Optically active a-methylene-y-butyrolactones fused to five or six-membered carbocyclic ring were synthesized in 64-9270 enantiomeric excess using the intramolecular Hosomi reaction of w-formylated p-(chiral)akqcarbonylallylsilanes.

In 1987 we reported a facile synthesis of a-methylene-y-lactones fused to five or six-membered carbccyclic ring system employing the intramolecular "Hosomi reaction" 2 of wformylated P-ethoxycarbonylallylsilanes (I;

R=Et,n=1,2).3 (Eq. 1) In this paper we report on the asymmetric synthesis of the optically active a-methylene-ylactones fused to five or six-membered carbocyclic ring by the use of this methodology.

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