Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system

Nicholas Voute; Douglas Philp; Alexandra M. Z. Slawin; Nicholas J. Westwood

doi:10.1039/b915677a

Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system

Nicholas Voute, Douglas Philp, Alexandra M. Z. Slawin, Nicholas J. Westwood

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

Abstract

A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of natural products.

Original language	English
Pages (from-to)	442-450
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	8
Issue number	2
Early online date	26 Nov 2009
DOIs	https://doi.org/10.1039/b915677a
Publication status	Published - 2010

Keywords

ENANTIOSELECTIVE TOTAL-SYNTHESIS
TRANSITION-STATE STRUCTURE
QUATERNARY CARBON CENTERS
SYNTHETIC APPROACH
CALYCANTHACEOUS ALKALOIDS
PENICILLIUM-EXPANSUM
BIOMIMETIC APPROACH
TANDEM OLEFINATION
ORGANIC-SYNTHESIS
RING-SYSTEM

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abstract = "A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of natural products.",

keywords = "ENANTIOSELECTIVE TOTAL-SYNTHESIS, TRANSITION-STATE STRUCTURE, QUATERNARY CARBON CENTERS, SYNTHETIC APPROACH, CALYCANTHACEOUS ALKALOIDS, PENICILLIUM-EXPANSUM, BIOMIMETIC APPROACH, TANDEM OLEFINATION, ORGANIC-SYNTHESIS, RING-SYSTEM",

author = "Nicholas Voute and Douglas Philp and Slawin, {Alexandra M. Z.} and Westwood, {Nicholas J.}",

year = "2010",

doi = "10.1039/b915677a",

language = "English",

volume = "8",

pages = "442--450",

journal = "Organic & Biomolecular Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system

AU - Voute, Nicholas

AU - Philp, Douglas

AU - Slawin, Alexandra M. Z.

AU - Westwood, Nicholas J.

PY - 2010

Y1 - 2010

N2 - A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of natural products.

AB - A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of natural products.

KW - ENANTIOSELECTIVE TOTAL-SYNTHESIS

KW - TRANSITION-STATE STRUCTURE

KW - QUATERNARY CARBON CENTERS

KW - SYNTHETIC APPROACH

KW - CALYCANTHACEOUS ALKALOIDS

KW - PENICILLIUM-EXPANSUM

KW - BIOMIMETIC APPROACH

KW - TANDEM OLEFINATION

KW - ORGANIC-SYNTHESIS

KW - RING-SYSTEM

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U2 - 10.1039/b915677a

DO - 10.1039/b915677a

M3 - Article

SN - 1477-0539

VL - 8

SP - 442

EP - 450

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 2

ER -

Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system

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Keywords

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