Primary-amine-catalyzed enantioselective intramolecular aldolizations

Jian Zhou; Vijay Wakchaure; Philip Kraft; Benjamin List

doi:10.1002/anie.200802497

Primary-amine-catalyzed enantioselective intramolecular aldolizations

Jian Zhou^*
, Vijay Wakchaure
, Philip Kraft
, Benjamin List

^*Corresponding author for this work

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

150 Scopus citations

Abstract

Aldol cyclodehydration of 4-substituted-2,6-heptanediones leads to enantiomerically enriched 5-substituted-3-methyl-2-cyclohexene-1-ones, which serve as perfume ingredients and valuable synthetic building blocks.Primary amines derived from cinchona alkaloids in combination with acetic acid are efficient catalysts for this transformation, which deliver both enantiomers of the celery ketone.

Original language	English
Pages (from-to)	7656-7658
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	40
DOIs	https://doi.org/10.1002/anie.200802497
State	Published - 22 Sep 2008
Externally published	Yes

Keywords

Aldol reaction
Asymmetric catalysis
Bifunctional catalysis
Enamines
Organocatalysis

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10.1002/anie.200802497

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title = "Primary-amine-catalyzed enantioselective intramolecular aldolizations",

abstract = "Aldol cyclodehydration of 4-substituted-2,6-heptanediones leads to enantiomerically enriched 5-substituted-3-methyl-2-cyclohexene-1-ones, which serve as perfume ingredients and valuable synthetic building blocks.Primary amines derived from cinchona alkaloids in combination with acetic acid are efficient catalysts for this transformation, which deliver both enantiomers of the celery ketone.",

keywords = "Aldol reaction, Asymmetric catalysis, Bifunctional catalysis, Enamines, Organocatalysis",

author = "Jian Zhou and Vijay Wakchaure and Philip Kraft and Benjamin List",

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AU - Zhou, Jian

AU - Wakchaure, Vijay

AU - Kraft, Philip

AU - List, Benjamin

PY - 2008/9/22

Y1 - 2008/9/22

N2 - Aldol cyclodehydration of 4-substituted-2,6-heptanediones leads to enantiomerically enriched 5-substituted-3-methyl-2-cyclohexene-1-ones, which serve as perfume ingredients and valuable synthetic building blocks.Primary amines derived from cinchona alkaloids in combination with acetic acid are efficient catalysts for this transformation, which deliver both enantiomers of the celery ketone.

AB - Aldol cyclodehydration of 4-substituted-2,6-heptanediones leads to enantiomerically enriched 5-substituted-3-methyl-2-cyclohexene-1-ones, which serve as perfume ingredients and valuable synthetic building blocks.Primary amines derived from cinchona alkaloids in combination with acetic acid are efficient catalysts for this transformation, which deliver both enantiomers of the celery ketone.

KW - Aldol reaction

KW - Asymmetric catalysis

KW - Bifunctional catalysis

KW - Enamines

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/54649084880

U2 - 10.1002/anie.200802497

DO - 10.1002/anie.200802497

M3 - 文章

AN - SCOPUS:54649084880

SN - 1433-7851

VL - 47

SP - 7656

EP - 7658

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -

Primary-amine-catalyzed enantioselective intramolecular aldolizations

Abstract

Keywords

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