[3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer

Siya Le, Ji Li, Jian Feng, Zuxiao Zhang, Yihui Bai, Zheliang Yuan and Gangguo Zhu ()
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Siya Le: Zhejiang Normal University
Ji Li: Zhejiang Normal University
Jian Feng: Zhejiang Normal University
Zuxiao Zhang: Zhejiang Normal University
Yihui Bai: Zhejiang Normal University
Zheliang Yuan: Zhejiang Normal University
Gangguo Zhu: Zhejiang Normal University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract [3+2] Cycloaddition is a step- and atom-economic method for the synthesis of five-membered rings. Despite the great success of 1,3-dipolar cycloadditions, the radical [3+2] annulation of alkynes remains a formidable challenge. Herein, a photoinduced decatungstate-catalyzed [3+2] cycloaddition of various internal alkynes using abundant aliphatic aldehydes as a three-carbon synthon is developed, producing elaborate cyclopentanones in 100% atom economy with excellent site-, regio-, and diastereoselectivity under mild conditions. The catalytic cycle consists of hydrogen atom abstraction from aldehydes, radical addition, 1,5-hydrogen atom transfer, anti-Baldwin 5-endo-trig cyclization, and back hydrogen abstraction. The power of this method is showcased by the late-stage elaboration of medicinally relevant molecules and total or formal synthesis of (±)-β-cuparenone, (±)-laurokamurene B, and (±)-cuparene.

Date: 2022
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DOI: 10.1038/s41467-022-32467-x

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