Palladium-Catalyzed Asymmetric Cycloaddition/Cope Rearrangement Relay: Synthesis of Chiral Endocyclic Allenes

Bin Shi; Wen-Jing Xiao; Liang-Qiu Lu

doi:10.1055/a-2072-3025

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(16): 1845-1851
DOI: 10.1055/a-2072-3025

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Palladium-Catalyzed Asymmetric Cycloaddition/Cope Rearrangement Relay: Synthesis of Chiral Endocyclic Allenes

Bin Shi

^aCCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China

,

Wen-Jing Xiao

^aCCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China

,

Liang-Qiu Lu∗

^aCCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, Gansu 730000, P. R. of China

^bSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. of China

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Abstract

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Abstract

The synthesis of chiral endocyclic allenes, especially the medium-sized ones, remains a challenge in allene chemistry due to unfavorable tension and difficult stereocontrol. Herein, an efficient protocol for the construction of chiral nine-membered endocyclic allenes via palladium-catalyzed asymmetric cycloaddition/Cope rearrangement relay of vinyl carbonates with activated enynes is highlighted. This process provides rapid access to a variety of chiral nine-membered endocyclic allenes in good yields with excellent enantioselectivities. In particular, a chiral P,S-ligand shows good performance on stereoinduction, generating central and axial chirality in a single transformation, which is rationalized by DFT calculations and by a proposed transition state.

1 Introduction

2 Pd-Catalyzed Asymmetric Cycloaddition/Cope Rearrangement Relay

3 Plausible Mechanism and Stereochemical Outcome

4 Conclusion and Outlook

Key words

chiral allene - medium-sized ring - cycloaddition - Cope rearrangement - asymmetric catalysis

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Referenzen

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