Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (-)-Oseltamivir

Jiang Weng; Yong Bo Li; Rui Bin Wang; Gui Lu

doi:10.1002/cctc.201200124

Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (-)-Oseltamivir

Jiang Weng, Yong Bo Li, Rui Bin Wang, Gui Lu^*

^*Corresponding author for this work

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

37 Scopus citations

Abstract

Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (-)-oseltamivir was accomplished in only five steps: two separate one-pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes.

Original language	English
Pages (from-to)	1007-1012
Number of pages	6
Journal	ChemCatChem
Volume	4
Issue number	7
DOIs	https://doi.org/10.1002/cctc.201200124
State	Published - Jul 2012
Externally published	Yes

Keywords

Asymmetric synthesis
Michael addition
Nitroenamines
Organocatalysis
Oseltamivir

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10.1002/cctc.201200124

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title = "Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (-)-Oseltamivir",

abstract = "Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (-)-oseltamivir was accomplished in only five steps: two separate one-pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes.",

keywords = "Asymmetric synthesis, Michael addition, Nitroenamines, Organocatalysis, Oseltamivir",

author = "Jiang Weng and Li, {Yong Bo} and Wang, {Rui Bin} and Gui Lu",

year = "2012",

month = jul,

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T1 - Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes

T2 - Short and Efficient Asymmetric Synthesis of (-)-Oseltamivir

AU - Weng, Jiang

AU - Li, Yong Bo

AU - Wang, Rui Bin

AU - Lu, Gui

PY - 2012/7

Y1 - 2012/7

N2 - Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (-)-oseltamivir was accomplished in only five steps: two separate one-pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes.

AB - Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (-)-oseltamivir was accomplished in only five steps: two separate one-pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes.

KW - Asymmetric synthesis

KW - Michael addition

KW - Nitroenamines

KW - Organocatalysis

KW - Oseltamivir

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DO - 10.1002/cctc.201200124

M3 - 文章

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SN - 1867-3880

VL - 4

SP - 1007

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JO - ChemCatChem

JF - ChemCatChem

IS - 7

ER -

Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (-)-Oseltamivir

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Keywords

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