alpha-Alkenoyl Ketene S,S-Acetal-Based Multicomponent Reaction: An Efficient Approach for the Selective Construction of Polyfunctionalized Cyclohexanones

作者：Ma Yuhui; Wang Mang^*; Li Dan; Bekturhun Bahargul; Liu Jun; Liu Qun

来源：Journal of Organic Chemistry, 2009, 74(8): 3116-3121.

DOI：10.1021/jo900217g

A versatile multicomponent reaction based on the new four-carbon synthons alpha-alkenoyl ketene S,S-acetals 1 has been developed. This three-component reaction of readily available alpha-alkenoyl ketene S,S-acetals 1 with aldehydes 2 and active methylene compounds 3 proceeds smoothly in acidic medium (glacial acetic acid in tetrahydrofuran) to give various polyfunctionalized cyclohexanones 4, 5, and 6 in a highly regio- and diastereoselective manner with good to excellent yields. The reaction can tolerate a broad range of substituents in the three components involved and is proposed to proceed via a tandem Knoevenagel-intermolecular Michael-intramolecular Michael sequence. As an extension of the synthetic application of polyfunctionalized cyclohexanones obtained, unsymmetrical biaryls 7 were synthesized in almost quantitative yields by simple transformations of the corresponding cycloadducts 6.

• 出版日期2009-4-17
• 单位东北师范大学