Recognition-induced Acceleration and Regiocontrol of a [3+2] Dipolar CycloadditionReaction

SJ Howell; Douglas Philp; N Spencer

Recognition-induced Acceleration and Regiocontrol of a [3+2] Dipolar CycloadditionReaction

SJ Howell, Douglas Philp, N Spencer

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

Abstract

The rational design of a recognition-based system that is capable of accelerating and controlling the regiochemical outcome of a dipolar cycloaddition reaction between an azide and an alkyne is presented. The origins of the acceleration and control of the cycloaddition reactions are rationalized-using molecular mechanics calculations-in terms of the formation of a complex between the reagents which organizes and orients them prior to reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	4945-4954
Number of pages	10
Journal	Tetrahedron
Volume	57
Publication status	Published - 4 Jun 2001

Keywords

azides
cycloaddition
kinetics
molecular recognition
DIELS-ALDER REACTION
INTRAMOLECULAR REACTIONS
CATALYSIS
ACCELERATION
ENERGETICS
MIMICS
MODELS

Cite this

@article{c8ee09c899a8471fa69ff16e28e694c3,

title = "Recognition-induced Acceleration and Regiocontrol of a [3+2] Dipolar CycloadditionReaction",

abstract = "The rational design of a recognition-based system that is capable of accelerating and controlling the regiochemical outcome of a dipolar cycloaddition reaction between an azide and an alkyne is presented. The origins of the acceleration and control of the cycloaddition reactions are rationalized-using molecular mechanics calculations-in terms of the formation of a complex between the reagents which organizes and orients them prior to reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "azides, cycloaddition, kinetics, molecular recognition, DIELS-ALDER REACTION, INTRAMOLECULAR REACTIONS, CATALYSIS, ACCELERATION, ENERGETICS, MIMICS, MODELS",

author = "SJ Howell and Douglas Philp and N Spencer",

year = "2001",

month = jun,

day = "4",

language = "English",

volume = "57",

pages = "4945--4954",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

}

TY - JOUR

T1 - Recognition-induced Acceleration and Regiocontrol of a [3+2] Dipolar CycloadditionReaction

AU - Howell, SJ

AU - Philp, Douglas

AU - Spencer, N

PY - 2001/6/4

Y1 - 2001/6/4

N2 - The rational design of a recognition-based system that is capable of accelerating and controlling the regiochemical outcome of a dipolar cycloaddition reaction between an azide and an alkyne is presented. The origins of the acceleration and control of the cycloaddition reactions are rationalized-using molecular mechanics calculations-in terms of the formation of a complex between the reagents which organizes and orients them prior to reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - The rational design of a recognition-based system that is capable of accelerating and controlling the regiochemical outcome of a dipolar cycloaddition reaction between an azide and an alkyne is presented. The origins of the acceleration and control of the cycloaddition reactions are rationalized-using molecular mechanics calculations-in terms of the formation of a complex between the reagents which organizes and orients them prior to reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - azides

KW - cycloaddition

KW - kinetics

KW - molecular recognition

KW - DIELS-ALDER REACTION

KW - INTRAMOLECULAR REACTIONS

KW - CATALYSIS

KW - ACCELERATION

KW - ENERGETICS

KW - MIMICS

KW - MODELS

UR - https://www.scopus.com/pages/publications/0035806175

M3 - Article

SN - 0040-4020

VL - 57

SP - 4945

EP - 4954

JO - Tetrahedron

JF - Tetrahedron

ER -

Recognition-induced Acceleration and Regiocontrol of a [3+2] Dipolar CycloadditionReaction

Abstract

Keywords

Other files and links

Fingerprint

Cite this