Journal of Organic Chemistry p. 1605 - 1613 (2019)
Update date:2022-08-11
Topics:
Li, Lu
Yang, Zhao
Yang, Jiao
Zhang, Quanzheng
Tan, Qiuyuan
Zhang, Changhui
Zhang, Min
A neighboring hydroxyl group-assisted allylboration of 3-indolyl ketones with γ,γ-disubstituted allylboronic acids is reported, affording various 3-indolyl-substituted homoallylic alcohols in good yields with excellent diastereoselectivies (up to >20:1 dr). The hydroxyl group not only played a vital role in the challenging allylboration but was elaborated for the subsequent construction of a hapalindole cyclohexane core by a highly diastereoselective Lewis acid-catalyzed carbonyl-ene reaction. In the overall process, four contiguous stereogenic centers including two quaternary stereogenic centers were installed.
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