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. 2008 Jul 7;350(10):1569-1576.
doi: 10.1002/adsc.200800242.

Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents

Venukrishnan Komanduri  1 , Fernando Pedraza, Michael J Krische
Affiliations

Direct Copper-Free Domino Conjugate Addition-Cycloallylation using Organozinc Reagents

Venukrishnan Komanduri et al. Adv Synth Catal. .

Abstract

The Direct Approach: Enones possessing appendant allylic carbonates react directly with diorganozinc reagents in the presence of zinc diiodide [ZnI(2)] to provide 5- and 6-membered ring products of tandem or domino conjugate addition-cycloallylation in good to excellent yield. In a related copper-free transformation, allylic carbonates are found to engage in direct allylic substitution with diorganozinc reagents.

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Figures

Scheme 1
Scheme 1
Top: Stereochemical assignment of compounds 1b and 2b. Bottom: Proposed stereochemical model.
Scheme 2
Scheme 2
Direct substitution of allylic carbonates 8a, iso-8a, 9a, iso-9a, and 10a by diethylzinc.
See this image and copyright information in PMC

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References

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