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Synthesis 2009(22): 3719-3743  
DOI: 10.1055/s-0029-1217066
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Organosilicon Compounds as Water Scavengers in Reactions of Carbonyl Compounds

Dmitriy M. Volochnyuk*a,b, Sergey V. Ryabukhina, Andrey S. Plaskona, Oleksandr O. Grygorenkoa,c
a Enamine Ltd., Alexandra Matrosova Street 23, Kyiv 01103, Ukraine
Fax: +38(44)5024832; e-Mail: D.Volochnyuk@enamine.net;
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv 02660, Ukraine
c Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine
Further Information

Publication History

Received 16 July 2009
Publication Date:
22 October 2009 (online)

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Abstract

The literature data on the application of organosilicon compounds as water scavengers in reactions of carbonyl compounds is surveyed. The reactions leading to both carbon-carbon (in particular, aldol-type condensations) and carbon-nitrogen bond formation, the synthesis of iminium salts by elimination reactions and heterocyclizations are considered.

1 Introduction

2 Reactions Leading to Carbon-Carbon Bond Formation

2.1 Aldol-Type Condensations

2.2 Other Reactions

3 Reactions Leading to Carbon-Nitrogen Bond Formation

3.1 Two-Component Condensations

3.2 Three-Component Condensations

4 Formation of Iminium Salts by Elimination Reactions

5 Heterocyclizations

5.1 Synthesis of O- and O,N-Containing Heterocycles

5.2 Synthesis of Pyrimidines by Biginelli Reaction

5.3 Synthesis of Other N-Containing Heterocycles

5.4 Recyclization of 3-Formylchromones

6 Conclusions

Key words

carbonyl compounds - condensation - organosilicon compounds - water scavengers - chlorotrimethylsilane