A One-Pot, Base-Free Annelation Approach to alpha-Alkylidene-gamma-butyrolactones

Russell R. A. Kitson; Richard J. K. Taylor; John L. Wood

doi:10.1021/ol902191d

A One-Pot, Base-Free Annelation Approach to alpha-Alkylidene-gamma-butyrolactones

Russell R. A. Kitson, Richard J. K. Taylor, John L. Wood

Chemistry

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

Abstract

A novel annelation procedure has been developed for the conversion of gamma-hydoxy enones into alpha-alkylidene-gamma-butyrolactones. This one-pot method utilizes the Bestmann ylide (triphenylphosphoranylideneketene) and proceeds by way of acylation followed by an intramolecular conjugate addition/proton transfer/Wittig olefination sequence. The procedure is "base-free" and is useful for the preparation of a range of alpha-alkylidene-gamma-butyrolactones including alpha-methylene-gamma-butyrolactone examples, which can be particularly base-sensitive.

Original language	English
Pages (from-to)	5338-5341
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	22
DOIs	https://doi.org/10.1021/ol902191d
Publication status	Published - 19 Nov 2009

Keywords

(+)-PAEONILACTONE-B
OLEFINATION
YLIDES

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10.1021/ol902191d

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abstract = "A novel annelation procedure has been developed for the conversion of gamma-hydoxy enones into alpha-alkylidene-gamma-butyrolactones. This one-pot method utilizes the Bestmann ylide (triphenylphosphoranylideneketene) and proceeds by way of acylation followed by an intramolecular conjugate addition/proton transfer/Wittig olefination sequence. The procedure is {"}base-free{"} and is useful for the preparation of a range of alpha-alkylidene-gamma-butyrolactones including alpha-methylene-gamma-butyrolactone examples, which can be particularly base-sensitive.",

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AU - Taylor, Richard J. K.

AU - Wood, John L.

PY - 2009/11/19

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N2 - A novel annelation procedure has been developed for the conversion of gamma-hydoxy enones into alpha-alkylidene-gamma-butyrolactones. This one-pot method utilizes the Bestmann ylide (triphenylphosphoranylideneketene) and proceeds by way of acylation followed by an intramolecular conjugate addition/proton transfer/Wittig olefination sequence. The procedure is "base-free" and is useful for the preparation of a range of alpha-alkylidene-gamma-butyrolactones including alpha-methylene-gamma-butyrolactone examples, which can be particularly base-sensitive.

AB - A novel annelation procedure has been developed for the conversion of gamma-hydoxy enones into alpha-alkylidene-gamma-butyrolactones. This one-pot method utilizes the Bestmann ylide (triphenylphosphoranylideneketene) and proceeds by way of acylation followed by an intramolecular conjugate addition/proton transfer/Wittig olefination sequence. The procedure is "base-free" and is useful for the preparation of a range of alpha-alkylidene-gamma-butyrolactones including alpha-methylene-gamma-butyrolactone examples, which can be particularly base-sensitive.

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KW - OLEFINATION

KW - YLIDES

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

A One-Pot, Base-Free Annelation Approach to alpha-Alkylidene-gamma-butyrolactones

Abstract

Keywords

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