Volume 27, Issue 16
Preparative Organic Chemistry
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ChemInform Abstract: Chemoselective Aldol-Type Condensation of Silyl Enol Ethers and Acetals in 5 mol dm-3 Lithium Perchlorate-Diethyl Ether.

V. G. SARASWATHY

V. G. SARASWATHY

Dep. Chem., Indian Inst. Technol., Madras 600 036, India

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S. SANKARARAMAN

S. SANKARARAMAN

Dep. Chem., Indian Inst. Technol., Madras 600 036, India

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First published: April 16, 1996

Abstract

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ChemInform Abstract

Aldol type condensation of (cyclic) acetals, e.g. (I), (VI) or (VIII) with silyl enol ether (II) under mild Lewis-acidic conditions gives the corresponding aldol ethers with moderate diastereoselectivity. Under the same conditions the parent aldehydes and ketals fail to react. In contrast to (II), which reacts with aromatic and aliphatic acetals equally facile, the corresponding cyclopentenyl ether (IV) does not react with aromatic acetals even after prolonged reaction time.

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