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Evidence of Formation of an exo-π-Allyl Complex Intermediate in the Pd0-Catalyzed Alkylation of a Bicyclic Allylic Diacetate with Stabilized Carbon Nucleophiles

✍ Scribed by Jean Michel Brunel; Michel Maffei; Günter Muchow; Gérard Buono

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 295 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200005)2000:9<1799::aid-ejoc1799>3.0.co;2-b

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✦ Synopsis

The palladium(0)-catalyzed alkylation of 2,3-bis(acetoxymethyl)bicyclo[2.2.1]hepta-2,5-diene 1 with malonate-type enolates as nucleophiles is investigated. A monoalkylated product is formed first, and undergoes (depending on the nucleophile used) a second intramolecular reaction leading to [a]

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Experimental Evidence on the Existence o

Experimental Evidence on the Existence of an exo-π-Allyl Complex Intermediate in the Pd0-Catalyzed Alkylation of a Bicyclic Allylic Diacetate with Stabilized Nucleophiles

✍ Jean Michel Brunel; Michel Maffei; Günter Muchow; Gérard Buono 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 292 KB

The Pd 0 -catalyzed alkylation of 1 by sodiodimethylmalonate led to the formation of two tricyclic diastereomers 2a and 2b. The structure of the major endo diastereomer 2b has been Scheme 1. Pd 0 -catalyzed alkylation of allylic bicyclic diacetate 1 [a] E.

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