N-Bromosuccinimide (NBS) Catalyzed Highly Chemoselective Acetalization of Carbonyl Compounds Using Silylated Diols and Pentaerythritol under Neutral Aprotic Conditions

Abstract

Various types of carbonyl compounds are efficiently converted to their 1,3-dioxanes and pentaerythritol diacetals by the use of either 1,3-bistrimethylsiloxy propane (A) or 1,3-bistrimethylsilanyloxy-2,2-bistrimethylsilanyloxymethyl propane (D) and a catalytic amount of N-bromosuccinimide (3-10 mol%) under essentially neutral aprotic condition, respectively. A variety of functionalities such as both aliphatic and phenolic -OTBDMS, -OMe, -OBz, furan ring, double bonds and more significantly phenolic -OTHP survived under the present reaction condition. The efficient conversion of two α-tertiary ketones to their cyclic acetals was also achieved using the present protocol.

Key Words

N-bromosuccinimide - acetals - aprotic acetalization - 1,3-dioxanes - pentaerythritol diacetals

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