Increasing the efficiency of the transannular diels-alder strategy via palladium(II)-catalyzed macrocyclizations

Robert G. Iafe; Jonathan L. Kuo; Dustin G. Hochstatter; Tomomi Saga; Jonathan W. Turner; Craig A. Merlic

doi:10.1021/ol303394t

Increasing the efficiency of the transannular diels-alder strategy via palladium(II)-catalyzed macrocyclizations

Robert G. Iafe, Jonathan L. Kuo, Dustin G. Hochstatter, Tomomi Saga, Jonathan W. Turner, Craig A. Merlic

Chemistry

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

21 Scopus citations

Abstract

Palladium(II)-catalyzed macrocyclizations of bis(vinylboronate ester) compounds are demonstrated to provide a strategically efficient approach to transannular Diels-Alder reaction substrates. In several systems reported, the macrocycle is preorganized such that cycloaddition at room temperature occurs concomitantly with cyclization. Numerous advantages over palladium(0)-catalyzed cross-coupling approaches are demonstrated.

Original language	English (US)
Pages (from-to)	582-585
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	3
DOIs	https://doi.org/10.1021/ol303394t
State	Published - Feb 1 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol303394t

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title = "Increasing the efficiency of the transannular diels-alder strategy via palladium(II)-catalyzed macrocyclizations",

abstract = "Palladium(II)-catalyzed macrocyclizations of bis(vinylboronate ester) compounds are demonstrated to provide a strategically efficient approach to transannular Diels-Alder reaction substrates. In several systems reported, the macrocycle is preorganized such that cycloaddition at room temperature occurs concomitantly with cyclization. Numerous advantages over palladium(0)-catalyzed cross-coupling approaches are demonstrated.",

author = "Iafe, {Robert G.} and Kuo, {Jonathan L.} and Hochstatter, {Dustin G.} and Tomomi Saga and Turner, {Jonathan W.} and Merlic, {Craig A.}",

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T1 - Increasing the efficiency of the transannular diels-alder strategy via palladium(II)-catalyzed macrocyclizations

AU - Iafe, Robert G.

AU - Kuo, Jonathan L.

AU - Hochstatter, Dustin G.

AU - Saga, Tomomi

AU - Turner, Jonathan W.

AU - Merlic, Craig A.

PY - 2013/2/1

Y1 - 2013/2/1

N2 - Palladium(II)-catalyzed macrocyclizations of bis(vinylboronate ester) compounds are demonstrated to provide a strategically efficient approach to transannular Diels-Alder reaction substrates. In several systems reported, the macrocycle is preorganized such that cycloaddition at room temperature occurs concomitantly with cyclization. Numerous advantages over palladium(0)-catalyzed cross-coupling approaches are demonstrated.

AB - Palladium(II)-catalyzed macrocyclizations of bis(vinylboronate ester) compounds are demonstrated to provide a strategically efficient approach to transannular Diels-Alder reaction substrates. In several systems reported, the macrocycle is preorganized such that cycloaddition at room temperature occurs concomitantly with cyclization. Numerous advantages over palladium(0)-catalyzed cross-coupling approaches are demonstrated.

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U2 - 10.1021/ol303394t

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JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Increasing the efficiency of the transannular diels-alder strategy via palladium(II)-catalyzed macrocyclizations

Abstract

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