Tandem [4+2]/[3+2] Cycloadditions of 1,3,4-Oxadiazoles with Alkenes

D Margetic; P Troselj; Martin Johnston

doi:10.2174/157019311793979981

Tandem [4+2]/[3+2] Cycloadditions of 1,3,4-Oxadiazoles with Alkenes

D Margetic, P Troselj, Martin Johnston

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

23 Citations (Scopus)

Abstract

A review on the tandem [4+2]/[3+2] cycloaddition reactions of 1,3,4-oxadiazoles with alkenes is presented. This reaction presents a powerful synthetic tool in the construction of complex polycyclic molecules in a one-pot reaction. Special attention is paid to synthesis of [n]polynorbornane and oxanorbornyl systems. In continuation, a review on the 1,3,4-oxadiazole reactions used in stereoselective total synthesis of alkaloids is given. Both intermolecular and intramolecular tandem [4+2]/[3+2] reactions are discussed. Stereospecificities and mechanistic rationale of various reactions are supported by quantum-chemical calculations (RHF/6-31G*).

Original language	English
Pages (from-to)	49-65
Number of pages	17
Journal	Mini-Reviews in Organic Chemistry
Volume	8
Issue number	1
DOIs	https://doi.org/10.2174/157019311793979981
Publication status	Published - 2011

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title = "Tandem [4+2]/[3+2] Cycloadditions of 1,3,4-Oxadiazoles with Alkenes",

abstract = "A review on the tandem [4+2]/[3+2] cycloaddition reactions of 1,3,4-oxadiazoles with alkenes is presented. This reaction presents a powerful synthetic tool in the construction of complex polycyclic molecules in a one-pot reaction. Special attention is paid to synthesis of [n]polynorbornane and oxanorbornyl systems. In continuation, a review on the 1,3,4-oxadiazole reactions used in stereoselective total synthesis of alkaloids is given. Both intermolecular and intramolecular tandem [4+2]/[3+2] reactions are discussed. Stereospecificities and mechanistic rationale of various reactions are supported by quantum-chemical calculations (RHF/6-31G*).",

author = "D Margetic and P Troselj and Martin Johnston",

year = "2011",

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AU - Troselj, P

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PY - 2011

Y1 - 2011

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AB - A review on the tandem [4+2]/[3+2] cycloaddition reactions of 1,3,4-oxadiazoles with alkenes is presented. This reaction presents a powerful synthetic tool in the construction of complex polycyclic molecules in a one-pot reaction. Special attention is paid to synthesis of [n]polynorbornane and oxanorbornyl systems. In continuation, a review on the 1,3,4-oxadiazole reactions used in stereoselective total synthesis of alkaloids is given. Both intermolecular and intramolecular tandem [4+2]/[3+2] reactions are discussed. Stereospecificities and mechanistic rationale of various reactions are supported by quantum-chemical calculations (RHF/6-31G*).

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DO - 10.2174/157019311793979981

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JO - Mini-Reviews in Organic Chemistry

JF - Mini-Reviews in Organic Chemistry

IS - 1

ER -

Tandem [4+2]/[3+2] Cycloadditions of 1,3,4-Oxadiazoles with Alkenes

Abstract

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