Palladium-catalysed cyclisation of chiral carbohydrate-derived geminal diacetates

Cedric W. Holzapfel; Lizel Marais; Francois Toerien

doi:10.1016/S0040-4020(98)01155-7

Palladium-catalysed cyclisation of chiral carbohydrate-derived geminal diacetates

Cedric W. Holzapfel, Lizel Marais, Francois Toerien

Chemical Sciences

University of Johannesburg

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

15 Citations (Scopus)

Abstract

The Pd(0) and Pd(II)-catalysed cyclisation/functionalisation reactions of acyclic carbohydrate-derived 1,1-diacetoxy-2,7-diene and 1,1-diacetoxy-2- en-7-yne compounds proceeded in a stereospecific fashion to furnish chiral, multi-functionalised furanoid and cyclopentanoid products. The products contained valuable enolacetate moieties, which can be further elaborated to enable the facile entry to an array of substituted five membered ring compounds.

Original language	English
Pages (from-to)	3467-3478
Number of pages	12
Journal	Tetrahedron
Volume	55
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(98)01155-7
Publication status	Published - Mar 1999

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Palladium-catalysed cyclisation of chiral carbohydrate-derived geminal diacetates",

abstract = "The Pd(0) and Pd(II)-catalysed cyclisation/functionalisation reactions of acyclic carbohydrate-derived 1,1-diacetoxy-2,7-diene and 1,1-diacetoxy-2- en-7-yne compounds proceeded in a stereospecific fashion to furnish chiral, multi-functionalised furanoid and cyclopentanoid products. The products contained valuable enolacetate moieties, which can be further elaborated to enable the facile entry to an array of substituted five membered ring compounds.",

author = "Holzapfel, {Cedric W.} and Lizel Marais and Francois Toerien",

year = "1999",

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AU - Holzapfel, Cedric W.

AU - Marais, Lizel

AU - Toerien, Francois

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Y1 - 1999/3

N2 - The Pd(0) and Pd(II)-catalysed cyclisation/functionalisation reactions of acyclic carbohydrate-derived 1,1-diacetoxy-2,7-diene and 1,1-diacetoxy-2- en-7-yne compounds proceeded in a stereospecific fashion to furnish chiral, multi-functionalised furanoid and cyclopentanoid products. The products contained valuable enolacetate moieties, which can be further elaborated to enable the facile entry to an array of substituted five membered ring compounds.

AB - The Pd(0) and Pd(II)-catalysed cyclisation/functionalisation reactions of acyclic carbohydrate-derived 1,1-diacetoxy-2,7-diene and 1,1-diacetoxy-2- en-7-yne compounds proceeded in a stereospecific fashion to furnish chiral, multi-functionalised furanoid and cyclopentanoid products. The products contained valuable enolacetate moieties, which can be further elaborated to enable the facile entry to an array of substituted five membered ring compounds.

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U2 - 10.1016/S0040-4020(98)01155-7

DO - 10.1016/S0040-4020(98)01155-7

M3 - Article

AN - SCOPUS:0033105341

SN - 0040-4020

VL - 55

SP - 3467

EP - 3478

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Palladium-catalysed cyclisation of chiral carbohydrate-derived geminal diacetates

Abstract

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