Asymmetric Access to Boryl-Substituted Vicinal Aminoalcohols through Cu-Catalyzed Reductive Coupling

04 November 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Important biologically active organic compounds such as natural products and pharmaceuticals often contain multiple oxygen and nitrogen heteroatoms within their carbon framework. Furthermore, chiral 1,2-aminoalcohol substitution patterns are often present in such compounds. As a result, efficient methods to access the 1,2-aminoalcohol motif while installing additional functionality for subsequent diversification in a stereoselective manner is highly desirable. Towards this end, we report a strategy based on Cu-catalyzed enantioselective borylative aminoallylation of aldehydes using a N-substituted allene to access boryl-substituted 1,2-aminoalcohol synthons for diversification to chiral heteroatom-rich organic compounds. The reported reaction provides access to several different substitution patterns of chiral 1,2-aminoalcohol products from the same readily available starting materials with high enantioselectivity (>95:5 er).


reductive coupling


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.