Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives

Jinxing Ye; Darren J. Dixon; Peter S. Hynes

doi:10.1039/b508833j

Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives

Jinxing Ye, Darren J. Dixon, Peter S. Hynes

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

Abstract

A family of 9-amino(9-deoxy) epicinchonine derivatives, possessing a range of mono- and bidentate hydrogen bond donor groups at the 9-position, were synthesised and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to β-nitrostyrene; thiourea derivative 1e was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins. © The Royal Society of Chemistry 2005.

Original language	English
Pages (from-to)	4481-4483
Number of pages	2
Journal	Chemical Communications
Issue number	35
DOIs	https://doi.org/10.1039/b508833j
Publication status	Published - 21 Sept 2005

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title = "Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives",

abstract = "A family of 9-amino(9-deoxy) epicinchonine derivatives, possessing a range of mono- and bidentate hydrogen bond donor groups at the 9-position, were synthesised and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to β-nitrostyrene; thiourea derivative 1e was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins. {\textcopyright} The Royal Society of Chemistry 2005.",

author = "Jinxing Ye and Dixon, {Darren J.} and Hynes, {Peter S.}",

year = "2005",

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language = "English",

pages = "4481--4483",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives

AU - Ye, Jinxing

AU - Dixon, Darren J.

AU - Hynes, Peter S.

PY - 2005/9/21

Y1 - 2005/9/21

N2 - A family of 9-amino(9-deoxy) epicinchonine derivatives, possessing a range of mono- and bidentate hydrogen bond donor groups at the 9-position, were synthesised and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to β-nitrostyrene; thiourea derivative 1e was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins. © The Royal Society of Chemistry 2005.

AB - A family of 9-amino(9-deoxy) epicinchonine derivatives, possessing a range of mono- and bidentate hydrogen bond donor groups at the 9-position, were synthesised and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to β-nitrostyrene; thiourea derivative 1e was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins. © The Royal Society of Chemistry 2005.

U2 - 10.1039/b508833j

DO - 10.1039/b508833j

M3 - Article

SN - 1359-7345

SP - 4481

EP - 4483

JO - Chemical Communications

JF - Chemical Communications

IS - 35

ER -

Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives

Abstract

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