Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes

Derek R. Boyd; Mark Bell; Katherine S. Dunne; Brian Kelly; Paul J. Stevenson; John F. Malone; Christopher Allen

doi:10.1039/c1ob06599h

Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes

Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone, Christopher Allen

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

14 Citations (Scopus)

Abstract

The chemoenzymatic synthesis of a Lewis basic phosphine-phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene proceeds via a palladium-catalysed carbon-phosphorus bond coupling and a novel room temperature Arbuzov [2,3]-sigmatropic rearrangement of an allylic diphenylphosphinite. Allylation of aromatic aldehydes were catalysed by the Lewis basic organocatalyst giving homoallylic alcohols in up to 57% ee. This compound also functioned as a ligand for rhodium-catalysed asymmetric hydrogenation of acetamidoacrylate giving reduction products with ee values of up to 84%.

Original language	English
Pages (from-to)	1388-1395
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	7
Early online date	16 Nov 2011
DOIs	https://doi.org/10.1039/c1ob06599h
Publication status	Published - 21 Feb 2012

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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title = "Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes",

abstract = "The chemoenzymatic synthesis of a Lewis basic phosphine-phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene proceeds via a palladium-catalysed carbon-phosphorus bond coupling and a novel room temperature Arbuzov [2,3]-sigmatropic rearrangement of an allylic diphenylphosphinite. Allylation of aromatic aldehydes were catalysed by the Lewis basic organocatalyst giving homoallylic alcohols in up to 57% ee. This compound also functioned as a ligand for rhodium-catalysed asymmetric hydrogenation of acetamidoacrylate giving reduction products with ee values of up to 84%.",

author = "Boyd, {Derek R.} and Mark Bell and Dunne, {Katherine S.} and Brian Kelly and Stevenson, {Paul J.} and Malone, {John F.} and Christopher Allen",

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volume = "10",

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Chemoenzymatic synthesis of a mixed phosphine-phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes. / Boyd, Derek R.; Bell, Mark; Dunne, Katherine S.; Kelly, Brian; Stevenson, Paul J.; Malone, John F.; Allen, Christopher.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 7, 21.02.2012, p. 1388-1395.

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

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AU - Boyd, Derek R.

AU - Bell, Mark

AU - Dunne, Katherine S.

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AU - Stevenson, Paul J.

AU - Malone, John F.

AU - Allen, Christopher

PY - 2012/2/21

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AB - The chemoenzymatic synthesis of a Lewis basic phosphine-phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene proceeds via a palladium-catalysed carbon-phosphorus bond coupling and a novel room temperature Arbuzov [2,3]-sigmatropic rearrangement of an allylic diphenylphosphinite. Allylation of aromatic aldehydes were catalysed by the Lewis basic organocatalyst giving homoallylic alcohols in up to 57% ee. This compound also functioned as a ligand for rhodium-catalysed asymmetric hydrogenation of acetamidoacrylate giving reduction products with ee values of up to 84%.

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