Ketene Claisen rearrangement of camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres

VK Aggarwal; Alessandra Lattanzi; Daniel Fuentes Sanchez

doi:10.1039/b206857e

Ketene Claisen rearrangement of camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres

VK Aggarwal^*
, Alessandra Lattanzi
, Daniel Fuentes Sanchez

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

17 Citations (Scopus)

Abstract

Dichloroketene reacts, via a [3,3]-sigmatropic rearrangement, with camphor-derived 1,3-oxathianes of alpha,beta-unsaturated aldehydes to give macrocyclic thiolactones in high yield and with complete transfer of chirality. The rearrangement is stereospecific.

Translated title of the contribution	'Ketene Claisen Rearrangement of Camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres'
Original language	English
Pages (from-to)	2534-2535
Number of pages	2
Journal	Chemical Communications
Issue number	21
DOIs	https://doi.org/10.1039/b206857e
Publication status	Published - 2002

Research Groups and Themes

Organic & Biological

Keywords

ALLYL ETHERS
THIOETHERS
ALDEHYDES
MOLECULES

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10.1039/b206857e

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@article{085cddd79833426e99f93082cfed8e3f,

title = "Ketene Claisen rearrangement of camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres",

abstract = "Dichloroketene reacts, via a [3,3]-sigmatropic rearrangement, with camphor-derived 1,3-oxathianes of alpha,beta-unsaturated aldehydes to give macrocyclic thiolactones in high yield and with complete transfer of chirality. The rearrangement is stereospecific.",

keywords = "ALLYL ETHERS, THIOETHERS, ALDEHYDES, MOLECULES",

author = "VK Aggarwal and Alessandra Lattanzi and \{Fuentes Sanchez\}, Daniel",

year = "2002",

doi = "10.1039/b206857e",

language = "English",

pages = "2534--2535",

journal = "Chemical Communications",

issn = "1364-548X",

publisher = "Royal Society of Chemistry",

number = "21",

}

TY - JOUR

T1 - Ketene Claisen rearrangement of camphor-derived 1,3-oxathianes

T2 - complete control of tertiary and quaternary stereogenic centres

AU - Aggarwal, VK

AU - Lattanzi, Alessandra

AU - Fuentes Sanchez, Daniel

PY - 2002

Y1 - 2002

N2 - Dichloroketene reacts, via a [3,3]-sigmatropic rearrangement, with camphor-derived 1,3-oxathianes of alpha,beta-unsaturated aldehydes to give macrocyclic thiolactones in high yield and with complete transfer of chirality. The rearrangement is stereospecific.

AB - Dichloroketene reacts, via a [3,3]-sigmatropic rearrangement, with camphor-derived 1,3-oxathianes of alpha,beta-unsaturated aldehydes to give macrocyclic thiolactones in high yield and with complete transfer of chirality. The rearrangement is stereospecific.

KW - ALLYL ETHERS

KW - THIOETHERS

KW - ALDEHYDES

KW - MOLECULES

U2 - 10.1039/b206857e

DO - 10.1039/b206857e

M3 - Article (Academic Journal)

SN - 1364-548X

SN - 2050-5639

SP - 2534

EP - 2535

JO - Chemical Communications

JF - Chemical Communications

IS - 21

ER -

Ketene Claisen rearrangement of camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres

Abstract

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Keywords

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