Evans-Tishchenko Coupling of Heteroaryl Aldehydes

Philip D.  Dorgan; Jamie Durrani; A. N. Hulme; Manuel Cases-Thomas

doi:10.1021/jo1015689

Evans-Tishchenko Coupling of Heteroaryl Aldehydes

Philip D. Dorgan, Jamie Durrani, A. N. Hulme, Manuel Cases-Thomas

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

Abstract

The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with β-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99%) and good to excellent diastereoselectivity (90:10 f 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.

Original language	English
Pages (from-to)	7475–7478
Number of pages	4
Journal	The Journal of Organic Chemistry (JOC)
Volume	75
Issue number	21
DOIs	https://doi.org/10.1021/jo1015689
Publication status	Published - Nov 2010

Keywords / Materials (for Non-textual outputs)

Evans-Tishchenko
beta-hydroxy ketone
anti-1,3 diol
samarium

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http://pubs.acs.org/doi/abs/10.1021/jo1015689

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title = "Evans-Tishchenko Coupling of Heteroaryl Aldehydes",

abstract = "The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with β-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99\%) and good to excellent diastereoselectivity (90:10 f 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.",

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year = "2010",

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volume = "75",

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AU - Dorgan, Philip D.

AU - Durrani, Jamie

AU - Hulme, A. N.

AU - Cases-Thomas, Manuel

PY - 2010/11

Y1 - 2010/11

N2 - The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with β-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99%) and good to excellent diastereoselectivity (90:10 f 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.

AB - The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with β-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99%) and good to excellent diastereoselectivity (90:10 f 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.

KW - Evans-Tishchenko

KW - beta-hydroxy ketone

KW - anti-1,3 diol

KW - samarium

UR - https://www.scopus.com/pages/publications/78049492740

U2 - 10.1021/jo1015689

DO - 10.1021/jo1015689

M3 - Article

AN - SCOPUS:78049492740

SN - 0022-3263

VL - 75

SP - 7475

EP - 7478

JO - The Journal of Organic Chemistry (JOC)

JF - The Journal of Organic Chemistry (JOC)

IS - 21

ER -

Evans-Tishchenko Coupling of Heteroaryl Aldehydes

Abstract

Keywords / Materials (for Non-textual outputs)

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