Stereocontrolled palladium(0) catalysed cyclisation and cyclisation/carbonylation of pseudoglycal derivatives

Cedric W. Holzapfel; Gerhard J. Engelbrecht; Lizel Marais; Francois Toerien

doi:10.1016/S0040-4020(97)00012-4

Stereocontrolled palladium(0) catalysed cyclisation and cyclisation/carbonylation of pseudoglycal derivatives

Cedric W. Holzapfel
, Gerhard J. Engelbrecht
, Lizel Marais
, Francois Toerien

Chemical Sciences

University of Johannesburg

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

20 Citations (Scopus)

Abstract

Pd(0) catalysed cyclisations of selected pseudoglycal 1,6-diene and 1,6-enyne derivatives provided annulated pyranoside products in a highly stereospecific fashion. Carbon monoxide insertion reactions of the cyclised σ-Pd intermediates afforded bicyclic carboxylic acids and/or bis-annulated cyclopentanone or -pentenane monosaccharide derivatives with the concomitant stereocontrolled formation of up to three C-C bonds.

Original language	English
Pages (from-to)	3957-3974
Number of pages	18
Journal	Tetrahedron
Volume	53
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(97)00012-4
Publication status	Published - 17 Mar 1997

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Stereocontrolled palladium(0) catalysed cyclisation and cyclisation/carbonylation of pseudoglycal derivatives",

abstract = "Pd(0) catalysed cyclisations of selected pseudoglycal 1,6-diene and 1,6-enyne derivatives provided annulated pyranoside products in a highly stereospecific fashion. Carbon monoxide insertion reactions of the cyclised σ-Pd intermediates afforded bicyclic carboxylic acids and/or bis-annulated cyclopentanone or -pentenane monosaccharide derivatives with the concomitant stereocontrolled formation of up to three C-C bonds.",

author = "Holzapfel, \{Cedric W.\} and Engelbrecht, \{Gerhard J.\} and Lizel Marais and Francois Toerien",

year = "1997",

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doi = "10.1016/S0040-4020(97)00012-4",

language = "English",

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T1 - Stereocontrolled palladium(0) catalysed cyclisation and cyclisation/carbonylation of pseudoglycal derivatives

AU - Holzapfel, Cedric W.

AU - Engelbrecht, Gerhard J.

AU - Marais, Lizel

AU - Toerien, Francois

PY - 1997/3/17

Y1 - 1997/3/17

N2 - Pd(0) catalysed cyclisations of selected pseudoglycal 1,6-diene and 1,6-enyne derivatives provided annulated pyranoside products in a highly stereospecific fashion. Carbon monoxide insertion reactions of the cyclised σ-Pd intermediates afforded bicyclic carboxylic acids and/or bis-annulated cyclopentanone or -pentenane monosaccharide derivatives with the concomitant stereocontrolled formation of up to three C-C bonds.

AB - Pd(0) catalysed cyclisations of selected pseudoglycal 1,6-diene and 1,6-enyne derivatives provided annulated pyranoside products in a highly stereospecific fashion. Carbon monoxide insertion reactions of the cyclised σ-Pd intermediates afforded bicyclic carboxylic acids and/or bis-annulated cyclopentanone or -pentenane monosaccharide derivatives with the concomitant stereocontrolled formation of up to three C-C bonds.

UR - https://www.scopus.com/pages/publications/0031575856

U2 - 10.1016/S0040-4020(97)00012-4

DO - 10.1016/S0040-4020(97)00012-4

M3 - Article

AN - SCOPUS:0031575856

SN - 0040-4020

VL - 53

SP - 3957

EP - 3974

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Stereocontrolled palladium(0) catalysed cyclisation and cyclisation/carbonylation of pseudoglycal derivatives

Abstract

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