Title

The Effect of the Carbon Ligand on the Reaction of Organozinc Reagents in the Synthesis of Substituted 2,5-Dihydrofurans: A Rare Example of An Uncatalysed Allylic-Substitution Reaction Involving Alkyl Zinc Halides

Published In

European Journal of Organic Chemistry

Document Type

Citation

Publication Date

2000

Abstract

Organozinc halides derived from Grignard reagents behave differently in their reaction with ethyl (±±)-(2RS,3SR)-tetrahydro-4-methylene-2-phenyl-3-(phenylsulfonyl)furan-3-carboxylate (3) according to the hybridisation of the carbon ligand. During the development of short multi-component reactions for the synthesis of diverse functionalized ethyl 2,5-dihydrofuran-3-carboxylates it was discovered that aryl and vinyl zinc halides undergo clean reaction with 3 in the presence of Pd(PPh3)4. In contrast, when alkyl zinc halides are reacted with 3 in the presence of Pd(PPh3)4, reductive desulfonation of 3 is observed. Remarkably, in the absence of a transition metal catalyst, the allylic substitution of 3 with alkyl zinc halides proceeds cleanly and in moderate to good yield.

Rights

Copyright © 1999-2021 John Wiley & Sons, Inc.

Description

At the time of publication Mark Woods was affiliated with Université Claude Bernard Lyon 1

DOI

10.1002/(SICI)1099-0690(200005)2000:9<1711::AID-EJOC1711>3.0.CO;2-1

Persistent Identifier

https://archives.pdx.edu/ds/psu/36518

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