Enantioselective Synthesis of Chiral 1,4-Enynes via Palladium-Catalyzed Branch-Selective Allylic C–H Alkylation
We herein present the construction of a chiral 1,4-enyne featuring tertiary or quaternary stereogenic center via Pd-catalyzed branch-, enantio-, and diastereoselective allylic C–H alkylation. Alkynyl carbon bearing bulky substituents appeared to exhibit competitive reaction performance, and the desired chiral 1,4-enynes were obtained in up to 93% yield and with up to >20:1 b/l, >20:1 dr, and 98% ee. A gram-scale experiment, the feasible operation of benzothiazole ring, and the preparation of the key intermediate to access (+)-Breynolide and prostaglandin are represented as a demonstration of multifarious synthetic utility in chemical synthesis.
Authors
- Zhong‐Sheng Nong (ORCID: https://orcid.org/0000-0001-5042-5443)
- Zihan Lin (ORCID: https://orcid.org/0000-0002-1912-0729)
- Yazhou Lou (ORCID: https://orcid.org/0000-0002-4825-4638)
- Liu‐Zhu Gong (ORCID: https://orcid.org/0000-0001-6099-827X)
- Rui Liu (ORCID: https://orcid.org/0000-0002-8227-6064)
- Chenxi Wu
Institutions
- University of Science and Technology of China (CN)
- Anhui Medical University (CN)
- Hefei National Center for Physical Sciences at Nanoscale (CN)
Publication Details
- Journal
- ACS Catalysis
- Published
- 2024-09-23
- DOI
- https://doi.org/10.1021/acscatal.4c04642
- Citations
- 5
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- National Natural Science Foundation of China
- Anhui Medical University
- Natural Science Foundation of Anhui Province
- National Key Research and Development Program of China