Diastereoselective dimerisation of alkenylthiazolines: A combined synthetic and computational study

Ariane Beutler; Christopher D. Davies; Mark C. Elliott; NM Galea; Matthew S. Long; David J. Willock; John L.  Wood

doi:10.1002/ejoc.200500360

Diastereoselective dimerisation of alkenylthiazolines: A combined synthetic and computational study

Ariane Beutler, Christopher D. Davies, Mark C. Elliott, NM Galea, Matthew S. Long, David J. Willock, John L. Wood

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

Abstract

The acylative dimerisation of 2-alkenyl-1,3-thiazolines 1 gives compounds 3 and 8 upon treatment with trichloroacetyl chloride and trifluoroacetic anhydride, respectively. This reaction is completely diastereoselective, in particular giving only a single double-bond isomer. The scope of the reaction has been evaluated synthetically, while a computational study has elucidated the mechanism of the reaction and the origin of stereocontrol. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

Original language	English
Pages (from-to)	3791-3800
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2005
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.200500360
Publication status	Published - 26 Aug 2005
Externally published	Yes

Keywords

heterocycles
thiazolines
dimerisation
diastereoselectivity
semiempirical calculations
DIELS-ALDER REACTIONS
BATZELLADINE-A
HETEROCUMULENES
DERIVATIVES
ALDEHYDES

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title = "Diastereoselective dimerisation of alkenylthiazolines: A combined synthetic and computational study",

abstract = "The acylative dimerisation of 2-alkenyl-1,3-thiazolines 1 gives compounds 3 and 8 upon treatment with trichloroacetyl chloride and trifluoroacetic anhydride, respectively. This reaction is completely diastereoselective, in particular giving only a single double-bond isomer. The scope of the reaction has been evaluated synthetically, while a computational study has elucidated the mechanism of the reaction and the origin of stereocontrol. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).",

keywords = "heterocycles, thiazolines, dimerisation, diastereoselectivity, semiempirical calculations, DIELS-ALDER REACTIONS, BATZELLADINE-A, HETEROCUMULENES, DERIVATIVES, ALDEHYDES",

author = "Ariane Beutler and Davies, {Christopher D.} and Elliott, {Mark C.} and NM Galea and Long, {Matthew S.} and Willock, {David J.} and Wood, {John L.}",

year = "2005",

month = aug,

day = "26",

doi = "10.1002/ejoc.200500360",

language = "English",

volume = "2005",

pages = "3791--3800",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley",

number = "17",

}

TY - JOUR

T1 - Diastereoselective dimerisation of alkenylthiazolines

T2 - A combined synthetic and computational study

AU - Beutler, Ariane

AU - Davies, Christopher D.

AU - Elliott, Mark C.

AU - Galea, NM

AU - Long, Matthew S.

AU - Willock, David J.

AU - Wood, John L.

PY - 2005/8/26

Y1 - 2005/8/26

N2 - The acylative dimerisation of 2-alkenyl-1,3-thiazolines 1 gives compounds 3 and 8 upon treatment with trichloroacetyl chloride and trifluoroacetic anhydride, respectively. This reaction is completely diastereoselective, in particular giving only a single double-bond isomer. The scope of the reaction has been evaluated synthetically, while a computational study has elucidated the mechanism of the reaction and the origin of stereocontrol. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

AB - The acylative dimerisation of 2-alkenyl-1,3-thiazolines 1 gives compounds 3 and 8 upon treatment with trichloroacetyl chloride and trifluoroacetic anhydride, respectively. This reaction is completely diastereoselective, in particular giving only a single double-bond isomer. The scope of the reaction has been evaluated synthetically, while a computational study has elucidated the mechanism of the reaction and the origin of stereocontrol. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

KW - heterocycles

KW - thiazolines

KW - dimerisation

KW - diastereoselectivity

KW - semiempirical calculations

KW - DIELS-ALDER REACTIONS

KW - BATZELLADINE-A

KW - HETEROCUMULENES

KW - DERIVATIVES

KW - ALDEHYDES

U2 - 10.1002/ejoc.200500360

DO - 10.1002/ejoc.200500360

M3 - Article

SN - 1434-193X

VL - 2005

SP - 3791

EP - 3800

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Diastereoselective dimerisation of alkenylthiazolines: A combined synthetic and computational study

Abstract

Keywords

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