A rationally designed cocatalyst for the Morita-Baylis-Hillman reaction

Charlotte Ellen Susan Jones; Simon M. Turega; Matthew L. Clarke; Douglas Philp

doi:10.1016/j.tetlet.2008.05.037

A rationally designed cocatalyst for the Morita-Baylis-Hillman reaction

Charlotte Ellen Susan Jones, Simon M. Turega, Matthew L. Clarke, Douglas Philp

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

26 Citations (Scopus)

Abstract

The application of electronic structure calculations to a key transition state in the reaction manifold of the Morita-Baylis-Hillman reaction allows the design of two bis(thiourea) cocatalysts capable of accelerating this reaction through the hydrogen bond mediated recognition of both the nucleophile and the electrophile. (C) 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4666-4669
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2008.05.037
Publication status	Published - 28 Jul 2008

Keywords

DIELS-ALDER REACTIONS
HYDROGEN-BOND DONORS
ASYMMETRIC CATALYSIS
RATE ACCELERATION
SELF-REPLICATION
METAL-FREE
ORGANOCATALYSIS
RECOGNITION
MECHANISM
SOLVENTS

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10.1016/j.tetlet.2008.05.037

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title = "A rationally designed cocatalyst for the Morita-Baylis-Hillman reaction",

abstract = "The application of electronic structure calculations to a key transition state in the reaction manifold of the Morita-Baylis-Hillman reaction allows the design of two bis(thiourea) cocatalysts capable of accelerating this reaction through the hydrogen bond mediated recognition of both the nucleophile and the electrophile. (C) 2008 Elsevier Ltd. All rights reserved.",

keywords = "DIELS-ALDER REACTIONS, HYDROGEN-BOND DONORS, ASYMMETRIC CATALYSIS, RATE ACCELERATION, SELF-REPLICATION, METAL-FREE, ORGANOCATALYSIS, RECOGNITION, MECHANISM, SOLVENTS",

author = "Jones, {Charlotte Ellen Susan} and Turega, {Simon M.} and Clarke, {Matthew L.} and Douglas Philp",

year = "2008",

month = jul,

day = "28",

doi = "10.1016/j.tetlet.2008.05.037",

language = "English",

volume = "49",

pages = "4666--4669",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - A rationally designed cocatalyst for the Morita-Baylis-Hillman reaction

AU - Jones, Charlotte Ellen Susan

AU - Turega, Simon M.

AU - Clarke, Matthew L.

AU - Philp, Douglas

PY - 2008/7/28

Y1 - 2008/7/28

N2 - The application of electronic structure calculations to a key transition state in the reaction manifold of the Morita-Baylis-Hillman reaction allows the design of two bis(thiourea) cocatalysts capable of accelerating this reaction through the hydrogen bond mediated recognition of both the nucleophile and the electrophile. (C) 2008 Elsevier Ltd. All rights reserved.

AB - The application of electronic structure calculations to a key transition state in the reaction manifold of the Morita-Baylis-Hillman reaction allows the design of two bis(thiourea) cocatalysts capable of accelerating this reaction through the hydrogen bond mediated recognition of both the nucleophile and the electrophile. (C) 2008 Elsevier Ltd. All rights reserved.

KW - DIELS-ALDER REACTIONS

KW - HYDROGEN-BOND DONORS

KW - ASYMMETRIC CATALYSIS

KW - RATE ACCELERATION

KW - SELF-REPLICATION

KW - METAL-FREE

KW - ORGANOCATALYSIS

KW - RECOGNITION

KW - MECHANISM

KW - SOLVENTS

UR - http://www.scopus.com/inward/record.url?scp=45049083371&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.05.037

DO - 10.1016/j.tetlet.2008.05.037

M3 - Article

SN - 0040-4039

VL - 49

SP - 4666

EP - 4669

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

A rationally designed cocatalyst for the Morita-Baylis-Hillman reaction

Abstract

Keywords

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