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Asymmetric Photocatalytic C(sp 3 )-H Bond Addition to α-Substituted Acrylates.
- Source :
-
Organic letters [Org Lett] 2021 Apr 16; Vol. 23 (8), pp. 3157-3161. Date of Electronic Publication: 2021 Mar 29. - Publication Year :
- 2021
-
Abstract
- Asymmetric functionalization of inert C(sp <superscript>3</superscript> )-H bonds is a straightforward approach to realize versatile bond-forming events, allowing the precise assembly of molecular complexity with minimal functional manipulations. Here, we describe an asymmetric photocatalytic C(sp <superscript>3</superscript> )-H bond addition to α-substituted acrylates by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst and chiral phosphoric acid as a chiral proton-transfer shuttle. This protocol is supposed to occur via a radical/ionic relay process, including a TBADT-mediated HAT to cleave the inert C(sp <superscript>3</superscript> )-H bond, a 1,4-radical addition, a back hydrogen abstraction, and an enantioselective protonation. A variety of inert C-H bond patterns and α-substituted acrylates are well tolerated to enable the rapid synthesis of enantioenriched α-stereogenic esters from simple raw materials.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 23
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 33780255
- Full Text :
- https://doi.org/10.1021/acs.orglett.1c00801