Parallel Kinetic Resolution of Racemic Aldehydes by Use of                Asymmetric Horner-Wadsworth-Emmons Reactions

Torben Møller Pedersen; Jakob Feldthusen Jensen; Rikke Eva Humble; Tobias Rein; David Ackland Tanner; Kerstin Bodmann; Oliver Reiser

doi:10.1021/ol991387h

Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions

Torben Møller Pedersen, Jakob Feldthusen Jensen, Rikke Eva Humble, Tobias Rein, David Ackland Tanner, Kerstin Bodmann, Oliver Reiser

Universität Regensburg

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.

Original language	English
Journal	Organic Letters
Volume	2
Issue number	4
Pages (from-to)	535-538
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol991387h
Publication status	Published - 2000

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title = "Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions",

abstract = "A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution. ",

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doi = "10.1021/ol991387h",

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journal = "Organic Letters",

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AU - Pedersen, Torben Møller

AU - Jensen, Jakob Feldthusen

AU - Humble, Rikke Eva

AU - Rein, Tobias

AU - Tanner, David Ackland

AU - Bodmann, Kerstin

AU - Reiser, Oliver

PY - 2000

Y1 - 2000

N2 - A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.

AB - A racemic aldehyde can undergo parallel kinetic resolution (PKR) by simultaneous reaction with two different chiral phosphonates, differing either in the structure of the chiral auxiliary or in the structure of the phosphoryl group (i.e., one (E)- and one (Z)-selective reagent). This strategy allows conversion of a racemic aldehyde to two different, synthetically useful chiral products with essentially doubled material throughput and similar or improved selectivities as compared to conventional kinetic resolution.

U2 - 10.1021/ol991387h

DO - 10.1021/ol991387h

M3 - Journal article

SN - 1523-7060

VL - 2

SP - 535

EP - 538

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Parallel Kinetic Resolution of Racemic Aldehydes by Use of Asymmetric Horner-Wadsworth-Emmons Reactions

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