alpha,beta-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water

A.J. Boersma; B.L. Feringa; G. Roelfes

doi:10.1021/ol7015274

alpha,beta-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water

A.J. Boersma, B.L. Feringa, G. Roelfes

Synthetic Organic Chemistry

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

113 Citations (Scopus)

Abstract

alpha,beta-Unsaturated 2-acyl imidazoles are a novel and practical class of dienophiles for the DNA-based catalytic asymmetric Diels-Alder reaction in water. The Diels-Alder products are obtained with very high diastereoselectivities and enantioselectivities in the range of 83-98%. The catalytic reaction was performed on a 1.0 mmol scale, and the imidazole auxiliary was removed readily.

Original language	English
Pages (from-to)	3647-3650
Number of pages	4
Journal	Organic letters
Volume	9
Issue number	18
DOIs	https://doi.org/10.1021/ol7015274
Publication status	Published - 30-Aug-2007

Keywords

ARTIFICIAL METALLOENZYMES
ENANTIOSELECTIVE CATALYSIS
TRIFLATE COMPLEXES
BIOTIN-AVIDIN
HYDROGENATION
PROTEIN
DESIGN

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Cite this

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AU - Boersma, A.J.

AU - Feringa, B.L.

AU - Roelfes, G.

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N2 - alpha,beta-Unsaturated 2-acyl imidazoles are a novel and practical class of dienophiles for the DNA-based catalytic asymmetric Diels-Alder reaction in water. The Diels-Alder products are obtained with very high diastereoselectivities and enantioselectivities in the range of 83-98%. The catalytic reaction was performed on a 1.0 mmol scale, and the imidazole auxiliary was removed readily.

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KW - ARTIFICIAL METALLOENZYMES

KW - ENANTIOSELECTIVE CATALYSIS

KW - TRIFLATE COMPLEXES

KW - BIOTIN-AVIDIN

KW - HYDROGENATION

KW - PROTEIN

KW - DESIGN

U2 - 10.1021/ol7015274

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JO - Org.Lett.

JF - Org.Lett.

SN - 1523-7060

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