A Photoinduced Palladium-Catalyzed Cascade Reaction for the Synthesis of Chiral Piperidines with Chiral Amino Acid Derivatives and 1,3-Dienes

Abstract

A photoinduced palladium-catalyzed cascade reaction involving remote C(sp³)–H functionalization and intramolecular Tsuji–Trost annulation is developed. The reaction is proposed to proceed through a sequence involving the amidyl radical generation, 1,5-HAT-mediated alkyl radical formation, and subsequent difunctionalization of 1,3-dienes. Without the use of exogeneous photosensitizers and external oxidants, the reaction provided an efficient approach to multi-substituted chiral piperidines in high yields, employing readily available chiral amino acid derivatives and 1,3-dienes as the substrates. In most cases, the syn/anti ratio of the product could be further improved by treatment with catalytic amount of iron salt.

Key words

excited-state Pd catalysis - chiral piperidines - amino acids - 1,3-dienes - Tsuji–Trost annulation

Publication History

Received: 13 May 2023

Accepted after revision: 03 July 2023

Accepted Manuscript online:
03 July 2023

Article published online:
14 August 2023

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