✦ LIBER ✦

The Pummerer-type reaction mediated ring-opening of 2-alkyl substituted 1-[(2-methoxyethoxy)methoxy]-2-(phenylsulfinyl)cyclopropanes

✍ Scribed by Manat Pohmakotr; Panawan Moosophon; Somchai Pisutjaroenpong; Patoomratana Tuchinda; Vichai Reutrakul

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 61 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00723-7

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✦ Synopsis

a-Lithiated 1-[(2-methoxyethoxy)methoxy]-2-(phenylsylfinyl)cyclopropane reacted smoothly with alkylating agents to afford the corresponding a-alkylated cyclopropylsulfoxides, which underwent the Pummerer-type reaction mediated ring-opening at low temperature (-78°C) by employing TFAA/Pr i 2 NEt/CH 2 Cl 2 to give mixtures of b-(phenylthio)-a,band g,d-unsaturated aldehydes.

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