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2-alkoxy-3-methylenetetrahydrofurans by addition of 2-(bromozincmethyl)-3,3-dialkoxy-1-propenes to aldehydes and ketones followed by Pd(0)-catalyzed cyclization

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

Book ID
104589132
Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
137 KB
Volume
109
Category
Article
ISSN
0165-0513

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✦ Synopsis

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.

πŸ“œ SIMILAR VOLUMES

Conjugated exocyclic dienes by addition
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
✍ J. van der Louw; M. Slagt; J.L. van der Baan; F. Bickelhaupt; G.W. Klumpp πŸ“‚ Article πŸ“… 1989 πŸ› Elsevier Science 🌐 French βš– 187 KB

## 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.

Addition of 2-(phenoxymethyl)-2-propenyl
Addition of 2-(phenoxymethyl)-2-propenylmagnesium chloride to epoxides followed by Pd(0)-catalyzed cyclization: A one-pot synthesis of 3-methylenetetrahydropyrans
✍ J. van der Louw; G.J.J. Out; J.L. van der Baan; F.J.J. de Kanter; F. Bickelhaupt πŸ“‚ Article πŸ“… 1989 πŸ› Elsevier Science 🌐 French βš– 216 KB

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.