Asymmetric (4+1) Annulations by Cascade Allylation and Transient σ‐Alkyl‐Pd(II) Initiated Allylic Csp3−H Activation

Author:

Sun Haiyu1,He Hui2,Ni Shao‐Fei2,Guo Wusheng1ORCID

Affiliation:

1. Frontier Institute of Science and Technology (FIST) Xi'an Jiaotong University Yanxiang Road 99 Xi'an 710045 China

2. Department of Chemistry Shantou University Shantou 515063 China

Abstract

AbstractA unique Pd‐catalyzed approach for asymmetric (4+1) annulations via cascade allylation and transient σ‐alkyl‐Pd(II) initiated methylene Csp3−H activation is reported. The enolate fragment derived from the decarboxylation of vinyl methylene carbonate is crucial to stabilize the key intermediate. These reactions enable the synthesis of various useful dihydrobenzofurans with excellent enantioselectivity, typically >95 : 5 er, and exclusive (Z)‐stereoselectivity. Compared with the well‐established annulations via Heck‐type C−H activations, this protocol showcases a conceptually new way to generate σ‐alkyl‐Pd(II) species that could initiate challenging asymmetric Csp3−H activations.

Publisher

Wiley

Subject

General Medicine

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