Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides
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 / alkylationSource:
Tetrahedron, 2004, 60, 40, 8957-8966Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.1016/j.tet.2004.07.007
ISSN: 0040-4020
WoS: 000223935100021
Scopus: 2-s2.0-4444296427
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Maslak, Veselin AU - Matović, Radomir AU - Saičić, Radomir PY - 2004 UR - https://cherry.chem.bg.ac.rs/handle/123456789/660 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 - Pergamon-Elsevier Science Ltd, Oxford 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", 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 = "Pergamon-Elsevier Science Ltd, Oxford", 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.. (2004). Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-butanolides. in Tetrahedron Pergamon-Elsevier Science Ltd, Oxford., 60(40), 8957-8966. https://doi.org/10.1016/j.tet.2004.07.007
Maslak V, Matović R, Saičić R. 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, "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 . .