Stereoselective synthesis of cis-2-aryl- and 2-alkyl-1-chlorocyclopropanecarboxaldehydes

✍ Scribed by Guido Verniest; Filip Bombeke; O.G Kulinkovich; Norbert De Kimpe

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 87 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)02228-6

✦ Synopsis

The title compounds were stereoselectively synthesized via a semi-benzilic Favorskii rearrangement of 3-aryl-and 3-alkyl-2,2-dichlorocyclobutanols, obtained by stereoselective reduction of the corresponding cyclobutanones. This synthetic pathway, starting from the synthesis of 3-substituted-2,2-dichlorocyclobutanones can be performed in one day with total yields up to 60% after purification. Reduction of the cyclobutanones yielded only cis-3-substituted cyclobutanols. Taking into account the stereoselectivity of the rearrangement, 1-halocyclopropanecarboxaldehydes, of which very few articles have been published, can be seen as highly interesting building blocks for further elaboration.