Stereoselective Organocatalytic Synthesis of α,α-Difluoro-γ,γ-Disubstituted Butenals

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• 作者：Satoru Arimitsu ; Makoto Nakasone
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：81
• 期：15
• 页码：6707-6713
• 全文大小：389K
• 年卷期：0
• ISSN：1520-6904

文摘

A highly stereoselective reaction of α,α-difluoro-γ,γ-disubstituted butenals 2 bearing two different substituents at the γ position has been developed with an organocatalytic system of l-proline (30 mol %) and salicylic acid (60 mol %). This novel reaction demonstrated a wide substrate scope and excellent E stereoselectivity in most cases. The obtained difluorinated aldehyde 2a was applied as a useful synthetic precursor for constructing 3,3-disubstituted allylic difluoride moieties.