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Solvent-Free Methallylboration of Ketones Accelerated by tert-Alcohols

Yongda Zhang*, Ning Li, Navneet Goyal, Guisheng Li, Heewon Lee, Bruce Z. Lu and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877-0368, United States, Email: yongda.zhangboehringer-ingelheim.com

Y. Zhang, N. Li, N. Goyal, G. Li, H. Lee, B. Z. Lu, C. H. Senanayake, J. Org. Chem., 2013, 78, 5775-5781.

DOI: 10.1021/jo4006574 (free Supporting Information)


Abstract

A solvent- and metal-free process for the direct methallylboration of ketones with a stable B-methallylborinane is accelerated by tertiary alcohols. In the presence of 2.0 equiv of tert-amyl alcohol, the methallylation products were prepared at room temperature in excellent yields. The process offers simple operation, high efficiency, and mild reaction conditions.

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Key Words

homoallylic alcohols


ID: J42-Y2013