Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes

Wen Ming Zhou; Han Liu; Da Ming Du

doi:10.1021/ol800945e

Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes

Wen Ming Zhou, Han Liu, Da Ming Du^*

^*Corresponding author for this work

Peking University

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

82 Citations (Scopus)

Abstract

(Chemical Equation Presented) The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route torward the synthesis of optically active functionalized naphthoquinones.

Original language	English
Pages (from-to)	2817-2820
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	13
DOIs	https://doi.org/10.1021/ol800945e
Publication status	Published - 2008
Externally published	Yes

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10.1021/ol800945e

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title = "Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes",

abstract = "(Chemical Equation Presented) The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route torward the synthesis of optically active functionalized naphthoquinones.",

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AU - Liu, Han

AU - Du, Da Ming

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Y1 - 2008

N2 - (Chemical Equation Presented) The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route torward the synthesis of optically active functionalized naphthoquinones.

AB - (Chemical Equation Presented) The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route torward the synthesis of optically active functionalized naphthoquinones.

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Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes

Abstract

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