Highly enantioselective michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts

Wen Yang; Da Ming Du

doi:10.1021/ol102294g

Highly enantioselective michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts

Wen Yang
, Da Ming Du^*

^*Corresponding author for this work

Beijing Institute of Technology

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

307 Citations (Scopus)

Abstract

A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C), affording the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (93-96% ee) by the appropriate choice of organocatalysts.

Original language	English
Pages (from-to)	5450-5453
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	23
DOIs	https://doi.org/10.1021/ol102294g
Publication status	Published - 3 Dec 2010
Externally published	Yes

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title = "Highly enantioselective michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts",

abstract = "A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C), affording the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (93-96\% ee) by the appropriate choice of organocatalysts.",

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journal = "Organic Letters",

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AU - Yang, Wen

AU - Du, Da Ming

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Y1 - 2010/12/3

N2 - A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C), affording the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (93-96% ee) by the appropriate choice of organocatalysts.

AB - A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low catalyst loading under high temperature (80 °C), affording the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (93-96% ee) by the appropriate choice of organocatalysts.

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U2 - 10.1021/ol102294g

DO - 10.1021/ol102294g

M3 - Article

AN - SCOPUS:78650333733

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JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Highly enantioselective michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts

Abstract

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