Diels-alder reactions on solid supports

Jari Yli-Kauhaluoma (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

43 Citations (Scopus)

Abstract

The Diels–Alder reaction is a concerted [4π+2π] cycloaddition reaction of a conjugated diene and a dienophile. This reaction belongs to the larger class of pericyclic reactions, and provides several pathways towards the simultaneous construction of substituted cyclohexenes with a high degree of regioselectivity, diastereoselectivity and enantioselectivity. Surveys on Diels–Alder reactions can be found in several excellent review articles.1., 2., 3., 4. Since its discovery in 1928, the Diels–Alder reaction has been amongst the most important carbon–carbon bond forming reactions available.5 The development of solid-phase organic chemistry has progressed rapidly during recent years, and copious solid-phase synthesis methods have been utilised in combinatorial chemistry.6., 7. Therefore, it is not surprising that several examples of solid-supported Diels–Alder reactions have been reported recently in the literature. This review includes examples of many types of Diels–Alder reactions, including classical intermolecular, inverse electron demand, hetero and intramolecular Diels–Alder reactions that have been performed on solid—mostly polymeric—support. This review covers the literature until June 2000.
Original languageEnglish
Pages (from-to)7053-7071
Number of pages19
JournalTetrahedron
Volume57
Issue number33
DOIs
Publication statusPublished - 2001
MoE publication typeA1 Journal article-refereed

Fingerprint

Cyclohexenes
Organic Chemistry
Solid-Phase Synthesis Techniques
Cycloaddition Reaction
Electrons
Regioselectivity
Cycloaddition
Enantioselectivity
Surveys and Questionnaires

Cite this

Yli-Kauhaluoma, Jari. / Diels-alder reactions on solid supports. In: Tetrahedron. 2001 ; Vol. 57, No. 33. pp. 7053-7071.
@article{9ed8aeb1393b434abfd4e11f1ebf706c,
title = "Diels-alder reactions on solid supports",
abstract = "The Diels–Alder reaction is a concerted [4π+2π] cycloaddition reaction of a conjugated diene and a dienophile. This reaction belongs to the larger class of pericyclic reactions, and provides several pathways towards the simultaneous construction of substituted cyclohexenes with a high degree of regioselectivity, diastereoselectivity and enantioselectivity. Surveys on Diels–Alder reactions can be found in several excellent review articles.1., 2., 3., 4. Since its discovery in 1928, the Diels–Alder reaction has been amongst the most important carbon–carbon bond forming reactions available.5 The development of solid-phase organic chemistry has progressed rapidly during recent years, and copious solid-phase synthesis methods have been utilised in combinatorial chemistry.6., 7. Therefore, it is not surprising that several examples of solid-supported Diels–Alder reactions have been reported recently in the literature. This review includes examples of many types of Diels–Alder reactions, including classical intermolecular, inverse electron demand, hetero and intramolecular Diels–Alder reactions that have been performed on solid—mostly polymeric—support. This review covers the literature until June 2000.",
author = "Jari Yli-Kauhaluoma",
year = "2001",
doi = "10.1016/S0040-4020(01)00506-3",
language = "English",
volume = "57",
pages = "7053--7071",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "33",

}

Diels-alder reactions on solid supports. / Yli-Kauhaluoma, Jari (Corresponding Author).

In: Tetrahedron, Vol. 57, No. 33, 2001, p. 7053-7071.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Diels-alder reactions on solid supports

AU - Yli-Kauhaluoma, Jari

PY - 2001

Y1 - 2001

N2 - The Diels–Alder reaction is a concerted [4π+2π] cycloaddition reaction of a conjugated diene and a dienophile. This reaction belongs to the larger class of pericyclic reactions, and provides several pathways towards the simultaneous construction of substituted cyclohexenes with a high degree of regioselectivity, diastereoselectivity and enantioselectivity. Surveys on Diels–Alder reactions can be found in several excellent review articles.1., 2., 3., 4. Since its discovery in 1928, the Diels–Alder reaction has been amongst the most important carbon–carbon bond forming reactions available.5 The development of solid-phase organic chemistry has progressed rapidly during recent years, and copious solid-phase synthesis methods have been utilised in combinatorial chemistry.6., 7. Therefore, it is not surprising that several examples of solid-supported Diels–Alder reactions have been reported recently in the literature. This review includes examples of many types of Diels–Alder reactions, including classical intermolecular, inverse electron demand, hetero and intramolecular Diels–Alder reactions that have been performed on solid—mostly polymeric—support. This review covers the literature until June 2000.

AB - The Diels–Alder reaction is a concerted [4π+2π] cycloaddition reaction of a conjugated diene and a dienophile. This reaction belongs to the larger class of pericyclic reactions, and provides several pathways towards the simultaneous construction of substituted cyclohexenes with a high degree of regioselectivity, diastereoselectivity and enantioselectivity. Surveys on Diels–Alder reactions can be found in several excellent review articles.1., 2., 3., 4. Since its discovery in 1928, the Diels–Alder reaction has been amongst the most important carbon–carbon bond forming reactions available.5 The development of solid-phase organic chemistry has progressed rapidly during recent years, and copious solid-phase synthesis methods have been utilised in combinatorial chemistry.6., 7. Therefore, it is not surprising that several examples of solid-supported Diels–Alder reactions have been reported recently in the literature. This review includes examples of many types of Diels–Alder reactions, including classical intermolecular, inverse electron demand, hetero and intramolecular Diels–Alder reactions that have been performed on solid—mostly polymeric—support. This review covers the literature until June 2000.

U2 - 10.1016/S0040-4020(01)00506-3

DO - 10.1016/S0040-4020(01)00506-3

M3 - Article

VL - 57

SP - 7053

EP - 7071

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 33

ER -