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Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides

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2004
Authors
Maslak, Veselin
Matović, Radomir
Saičić, Radomir N.
Article (Published version)
Metadata
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Abstract
Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides, followed by acidic work-up, affords butanolides in moderate/good yields. With epihalohydrins the reaction is regioselective and occurs at the less substituted end of the epoxide; the gamma-haloalkyl-gamma-butanolides thus obtained can be further transformed into various products. (C) 2004 Elsevier Ltd. All rights reserved.
Keywords:
epoxides / ketene acetals / lactones / titanium and compounds / alkylation
Source:
Tetrahedron, 2004, 60, 40, 8957-8966
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd

DOI: 10.1016/j.tet.2004.07.007

ISSN: 0040-4020

WoS: 000223935100021

Scopus: 2-s2.0-4444296427
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31
29
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2768
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Maslak, Veselin
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2768
AB  - Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides, followed by acidic work-up, affords butanolides in moderate/good yields. With epihalohydrins the reaction is regioselective and occurs at the less substituted end of the epoxide; the gamma-haloalkyl-gamma-butanolides thus obtained can be further transformed into various products. (C) 2004 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides
VL  - 60
IS  - 40
SP  - 8957
EP  - 8966
DO  - 10.1016/j.tet.2004.07.007
ER  - 
@article{
author = "Maslak, Veselin and Matović, Radomir and Saičić, Radomir N.",
year = "2004",
abstract = "Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides, followed by acidic work-up, affords butanolides in moderate/good yields. With epihalohydrins the reaction is regioselective and occurs at the less substituted end of the epoxide; the gamma-haloalkyl-gamma-butanolides thus obtained can be further transformed into various products. (C) 2004 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides",
volume = "60",
number = "40",
pages = "8957-8966",
doi = "10.1016/j.tet.2004.07.007"
}
Maslak, V., Matović, R.,& Saičić, R. N.. (2004). Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 60(40), 8957-8966.
https://doi.org/10.1016/j.tet.2004.07.007
Maslak V, Matović R, Saičić RN. Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides. in Tetrahedron. 2004;60(40):8957-8966.
doi:10.1016/j.tet.2004.07.007 .
Maslak, Veselin, Matović, Radomir, Saičić, Radomir N., "Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides" in Tetrahedron, 60, no. 40 (2004):8957-8966,
https://doi.org/10.1016/j.tet.2004.07.007 . .

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