Pd(II)-Catalyzed Desymmetrizing gem-Dimethyl C(sp3)-H Alkenylation/Aza-Wacker Cyclization Directed by PIP Auxiliary

Le-Song Wu; Tao Zhou; Bing-Feng Shi

doi:10.1021/acs.orglett.4c01214

Pd(II)-Catalyzed Desymmetrizing gem-Dimethyl C(sp³)-H Alkenylation/Aza-Wacker Cyclization Directed by PIP Auxiliary

Org Lett. 2024 May 31;26(21):4457-4462. doi: 10.1021/acs.orglett.4c01214. Epub 2024 May 22.

Authors

Le-Song Wu¹, Tao Zhou^{1

2}, Bing-Feng Shi^{1

2

3}

Affiliations

¹ Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
² College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121, Zhejiang China.
³ College of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing 314001, China.

PMID: 38775281
DOI: 10.1021/acs.orglett.4c01214

Abstract

Desymmetrization of gem-dimethyl groups has been developed as an efficient pathway to achieve asymmetric C(sp³)-H functionalization. Herein, we described a Pd(II)-catalyzed desymmetrizing gem-dimethyl C(sp³)-H alkenylation/aza-Wacker cyclization directed by a bidentate 2-pyridinylisopropyl auxiliary. Chiral α-methyl γ-lactams were obtained in good yields (up to 82%) and high enantioselectivities (up to 91.5% ee).