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

19 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

Access to Document

10.1016/S0040-4020(97)00012-4

Cite this

@article{856ac24d21134454a82ea54556c29fe9,

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",

month = mar,

day = "17",

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

language = "English",

volume = "53",

pages = "3957--3974",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "11",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=0031575856&partnerID=8YFLogxK

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this