open access

https://hdl.handle.net/2115/92676

Boron-Catalyzed alpha-Functionalizations of Carboxylic Acids

英語

Enolate

2023-07

Wiley-Blackwell

Chemical record

23(7)

e202200273

Catalytic, chemoselective, and asymmetric alpha-functionalizations of carboxylic acids promise up-grading simple feedstock materials to value-added functional molecules, as well as late-stage structural diversifications of multifunctional molecules, such as drugs and their leads. In this personal account, we describe boron-catalyzed alpha-functionalizations of carboxylic acids developed in our group (five reaction types). The reversible boron carboxylate formation is key to the acidification of the alpha-protons and enolization using mild organic bases, allowing for chemoselective and asymmetric bond formations of carboxylic acids. The ligand effects on reactivity and stereoselectivity, substrate scopes, and mechanistic insights are summarized.

学術雑誌論文

Accepted Manuscript

This is the peer reviewed version of the following article: Y. Shimizu, M. Kanai, Chem. Rec. 2023, 23, e202200273., which has been published in final form at https://doi.org/10.1002/tcr.202200273. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

1527-8999