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Allylmetalation of 1-silylalkynes by 2-bromozincmethyl-2-propenyl ethers followed by pd(0)-catalyzed cyclization: A one-pot synthesis of 4-methylenecyclopentenes

✍ Scribed by J. van der Louw; J.L. van der Baan; F. Bickelhaupt; G.W. Klumpp

Book ID
104227678
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
226 KB
Volume
28
Category
Article
ISSN
0040-4039

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πŸ“œ SIMILAR VOLUMES

2-alkoxy-3-methylenetetrahydrofurans by
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## Abstract Reaction of 2‐(bromozincmethyl)‐3,3‐dialkoxy‐1‐propenes 2 with aldehydes and ketones afforded addition products 4 which underwent Pd(0)‐catalyzed cyclization to 2‐alkoxy‐3‐methylenetetrahydrofurans 5.

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Addition of 2-(phenoxymethyl)-2-propenylmagnesium chloride to epoxides afforded the ring opening products 3 which were converted by Pd(0) to 3-methylenetetrahydropyrans 4.

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Conjugated exocyclic dienes by addition of 2-(benzyloxymethyl)-3-(bromozincmethyl)-1,3-but adiene to aldehydes, ketones and imines followed by Pd(0)-catalyzed cyclization
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## Reaction of 2-(benzyloxymethyl)-3-(bromozincmethyl)-I ,3-butadiene with aldehydes, ketones and imines afforded addition products 6, which underwent Pd(O)-catalyzed cyclization to the conjugated exocyclic dienes 7.