A dendritic active site: Catalysis of the Henry reaction

A V  Davis; M  Driffield; D K  Smith

A dendritic active site: Catalysis of the Henry reaction

A V Davis, M Driffield, D K Smith

Chemistry

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

Abstract

[GRAPHICS]

Dendrimers containing an encapsulated tertiary amine were prepared by coupling tris(2-aminoethyl)amine with dendritic branches derived from L-lysine. These dendrimers were used as catalysts in the Henry (nitroaldol) reaction between 4-nitrobenzaidehyde and nitroethane, and their catalytic performance was compared with that of triethylamine. Attachment of the dendritic shell alters the rate of reaction and influences the syn:anti ratio of products. It is proposed that the dendritic shell generates an encapsulated catalytically active site, mimicking the behavior of a protein superstructure.

Original language	English
Pages (from-to)	3075-3078
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	20
Publication status	Published - 4 Oct 2001

Keywords

MEMBRANE REACTOR
ENANTIOSELECTIVE CATALYSIS
CARBOSILANE DENDRIMERS
LIGANDS
COMPLEXES
PROBE

Cite this

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title = "A dendritic active site: Catalysis of the Henry reaction",

abstract = "[GRAPHICS]Dendrimers containing an encapsulated tertiary amine were prepared by coupling tris(2-aminoethyl)amine with dendritic branches derived from L-lysine. These dendrimers were used as catalysts in the Henry (nitroaldol) reaction between 4-nitrobenzaidehyde and nitroethane, and their catalytic performance was compared with that of triethylamine. Attachment of the dendritic shell alters the rate of reaction and influences the syn:anti ratio of products. It is proposed that the dendritic shell generates an encapsulated catalytically active site, mimicking the behavior of a protein superstructure.",

keywords = "MEMBRANE REACTOR, ENANTIOSELECTIVE CATALYSIS, CARBOSILANE DENDRIMERS, LIGANDS, COMPLEXES, PROBE",

author = "Davis, {A V} and M Driffield and Smith, {D K}",

year = "2001",

month = oct,

day = "4",

language = "English",

volume = "3",

pages = "3075--3078",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

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TY - JOUR

T1 - A dendritic active site: Catalysis of the Henry reaction

AU - Davis, A V

AU - Driffield, M

AU - Smith, D K

PY - 2001/10/4

Y1 - 2001/10/4

N2 - [GRAPHICS]Dendrimers containing an encapsulated tertiary amine were prepared by coupling tris(2-aminoethyl)amine with dendritic branches derived from L-lysine. These dendrimers were used as catalysts in the Henry (nitroaldol) reaction between 4-nitrobenzaidehyde and nitroethane, and their catalytic performance was compared with that of triethylamine. Attachment of the dendritic shell alters the rate of reaction and influences the syn:anti ratio of products. It is proposed that the dendritic shell generates an encapsulated catalytically active site, mimicking the behavior of a protein superstructure.

AB - [GRAPHICS]Dendrimers containing an encapsulated tertiary amine were prepared by coupling tris(2-aminoethyl)amine with dendritic branches derived from L-lysine. These dendrimers were used as catalysts in the Henry (nitroaldol) reaction between 4-nitrobenzaidehyde and nitroethane, and their catalytic performance was compared with that of triethylamine. Attachment of the dendritic shell alters the rate of reaction and influences the syn:anti ratio of products. It is proposed that the dendritic shell generates an encapsulated catalytically active site, mimicking the behavior of a protein superstructure.

KW - MEMBRANE REACTOR

KW - ENANTIOSELECTIVE CATALYSIS

KW - CARBOSILANE DENDRIMERS

KW - LIGANDS

KW - COMPLEXES

KW - PROBE

M3 - Article

SN - 1523-7060

VL - 3

SP - 3075

EP - 3078

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -