Direct Catalytic Enantioselective C(sp <sup>2</sup> )–H Allylation of Acrylic Acids: Modular Access to Chiral 1,4-Skipped Dienes
The direct enantioselective C-H functionalization of carboxylic acids represents a formidable yet highly appealing goal in synthesis, offering efficient access to chiral molecules from abundant feedstocks. Herein, we disclose a chiral Cp<sup>x</sup>Rh(III)-catalyzed strategy for the enantioselective alkenyl C-H allylation of acrylic acids. This transformation achieves a unique asymmetric C(sp<sup>2</sup>)-C(sp<sup>3</sup>) cross-coupling between two olefin coupling partners─acrylic acids and allyl acetates─delivering valuable enantioenriched 1,4-dienes with high efficiency and excellent enantioselectivity. This transformation exhibits a broad substrate scope and high functional group tolerance, with its synthetic utility demonstrated through scalable synthesis and diverse downstream derivatizations. This strategy establishes a versatile and practical approach to asymmetric alkenyl C-H functionalization for the convenient synthesis of valuable enantioenriched architectures.
Authors
- Mupeng Luo (ORCID: https://orcid.org/0000-0002-1222-7830)
- Qiang Zhou
- Juanjuan Wang (ORCID: https://orcid.org/0000-0003-2450-7554)
- Shouguo Wang (ORCID: https://orcid.org/0000-0001-8947-0946)
Institutions
- Shenzhen University (CN)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-12-17
- DOI
- https://doi.org/10.1021/jacs.5c17825
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00