The stereoselective synthesis of unsaturated nine-membered lactones using the Malherbe-Bellus variant of the Claisen rearrangement

Marcel R. Kling; Grant A. McNaughton-Smith; Richard J.K. Taylor

doi:10.1039/C39930001593

The stereoselective synthesis of unsaturated nine-membered lactones using the Malherbe-Bellus variant of the Claisen rearrangement

Marcel R. Kling, Grant A. McNaughton-Smith, Richard J.K. Taylor^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting Δ⁵-dichlorolactones are exclusively trans but dechlorination using Bu₃SnH-AlBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.

Original language	English
Pages (from-to)	1593-1595
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/C39930001593
Publication status	Published - 1 Dec 1993

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abstract = "The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting Δ5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH-AlBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.",

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AU - Taylor, Richard J.K.

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AB - The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting Δ5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH-AlBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.

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ER -

The stereoselective synthesis of unsaturated nine-membered lactones using the Malherbe-Bellus variant of the Claisen rearrangement

Abstract

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