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Synlett 2012; 23(9): 1283-1290
DOI: 10.1055/s-0031-1290490
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© Georg Thieme Verlag Stuttgart · New York

Cyclization Reactions of 1,1-Bis(trimethylsilyloxy)ketene Acetals

Tuan T. Dang
a   Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany, Fax: +49(381)4986412   Email: peter.langer@uni-rostock.de
b   Leibniz-Institute of Catalysis e. V. at the University of Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
,
Nazken K. Kelzhanova
a   Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany, Fax: +49(381)4986412   Email: peter.langer@uni-rostock.de
c   Al-Farabi Kazakh National University, Al-Farabi ave. 71, 050040 Almaty, Kazakhstan
,
Zharylkasyn A. Abilov
c   Al-Farabi Kazakh National University, Al-Farabi ave. 71, 050040 Almaty, Kazakhstan
,
Mirgul Zh. Turmukhanova
c   Al-Farabi Kazakh National University, Al-Farabi ave. 71, 050040 Almaty, Kazakhstan
,
Peter Langer*
a   Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany, Fax: +49(381)4986412   Email: peter.langer@uni-rostock.de
b   Leibniz-Institute of Catalysis e. V. at the University of Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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Further Information

Publication History

Received: 21 November 2011

Accepted after revision: 03 February 2012

Publication Date:
20 April 2012 (online)

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Abstract

1,1-Bis(trimethylsilyloxy)ketene acetals represent useful synthetic building blocks that can be regarded as masked carboxylic acid dianions. In recent years, a number of cyclization reactions of 1,1-bis(trimethylsilyloxy)ketene acetals have been reported that provide a convenient synthesis of various pharmacologically relevant heterocyclic products.

1 Introduction

2 Synthesis of Lactones

3 Synthesis of Cyclic Anhydrides

4 Synthesis of Lactone-Bridged N-Heterocycles

5 Synthesis of Lactone-Annulated N-Heterocycles

6 Conclusions

7 Acknowledgment

Key words

acetals - silyl enol ethers - cyclizations - regioselectivity - heterocycles