Mild Michael addition of glycine imines to aromatic nitroalkenes catalyzed by DBU with LiOTf as an additive

Wei Li; Han Liu; Da Ming Du

doi:10.1055/s-0028-1088210

Mild Michael addition of glycine imines to aromatic nitroalkenes catalyzed by DBU with LiOTf as an additive

Wei Li
, Han Liu
, Da Ming Du^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Peking University

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

13 Citations (Scopus)

Abstract

A mild Michael addition of glycine imines to aromatic-nitroalkenes catalyzed by 10 mol% DBU with LiOTf as an additive was developed. In most cases, the products could be obtained in good yields (up to 96%) with moderate to good diastereoselectivities (up to 10:1). The selectivity for syn adduct can be reversed to anti when the R group of glycine imines was changed from methyl or ethyl to tert-butyl.

Original language	English
Pages (from-to)	925-928
Number of pages	4
Journal	Synlett
Issue number	6
DOIs	https://doi.org/10.1055/s-0028-1088210
Publication status	Published - 2009

Keywords

Amino acids
Catalysis
DBU
Michael addition
Nitroalkene

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10.1055/s-0028-1088210

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title = "Mild Michael addition of glycine imines to aromatic nitroalkenes catalyzed by DBU with LiOTf as an additive",

abstract = "A mild Michael addition of glycine imines to aromatic-nitroalkenes catalyzed by 10 mol\% DBU with LiOTf as an additive was developed. In most cases, the products could be obtained in good yields (up to 96\%) with moderate to good diastereoselectivities (up to 10:1). The selectivity for syn adduct can be reversed to anti when the R group of glycine imines was changed from methyl or ethyl to tert-butyl.",

keywords = "Amino acids, Catalysis, DBU, Michael addition, Nitroalkene",

author = "Wei Li and Han Liu and Du, \{Da Ming\}",

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journal = "Synlett",

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AU - Li, Wei

AU - Liu, Han

AU - Du, Da Ming

PY - 2009

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N2 - A mild Michael addition of glycine imines to aromatic-nitroalkenes catalyzed by 10 mol% DBU with LiOTf as an additive was developed. In most cases, the products could be obtained in good yields (up to 96%) with moderate to good diastereoselectivities (up to 10:1). The selectivity for syn adduct can be reversed to anti when the R group of glycine imines was changed from methyl or ethyl to tert-butyl.

AB - A mild Michael addition of glycine imines to aromatic-nitroalkenes catalyzed by 10 mol% DBU with LiOTf as an additive was developed. In most cases, the products could be obtained in good yields (up to 96%) with moderate to good diastereoselectivities (up to 10:1). The selectivity for syn adduct can be reversed to anti when the R group of glycine imines was changed from methyl or ethyl to tert-butyl.

KW - Amino acids

KW - Catalysis

KW - DBU

KW - Michael addition

KW - Nitroalkene

UR - https://www.scopus.com/pages/publications/63849333390

U2 - 10.1055/s-0028-1088210

DO - 10.1055/s-0028-1088210

M3 - Article

AN - SCOPUS:63849333390

SN - 0936-5214

SP - 925

EP - 928

JO - Synlett

JF - Synlett

IS - 6

ER -

Mild Michael addition of glycine imines to aromatic nitroalkenes catalyzed by DBU with LiOTf as an additive

Abstract

Keywords

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