Asymmetric Synthesis of γ‑Secondary Amino Alcohols via a Borrowing-Hydrogen Cascade

Asymmetric Synthesis of γ‑Secondary Amino Alcohols via a Borrowing-Hydrogen Cascade

The borrowing-hydrogen (or hydrogen autotransfer) process, where the catalyst dehydrogenates a substrate and formally transfers the H atom to an unsaturated intermediate, is an atom-efficient and environmentally benign transformation. Described here is an example of an asymmetric borrowing-hydrogen...

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Veröffentlicht in:Organic letters 2020-09, Vol.22 (18), p.7278-7283
Hauptverfasser: Pan, Yupeng, You, Yipeng, He, Dongxu, Chen, Fumin, Chang, Xiaoyong, Jin, Ming Yu, Xing, Xiangyou
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container_issue 18
container_start_page 7278
container_title Organic letters
container_volume 22
creator Pan, Yupeng
You, Yipeng
He, Dongxu
Chen, Fumin
Chang, Xiaoyong
Jin, Ming Yu
Xing, Xiangyou
description The borrowing-hydrogen (or hydrogen autotransfer) process, where the catalyst dehydrogenates a substrate and formally transfers the H atom to an unsaturated intermediate, is an atom-efficient and environmentally benign transformation. Described here is an example of an asymmetric borrowing-hydrogen cascade for the formal anti-Markovnikov hydroamination of allyl alcohols to synthesize optically enriched γ-secondary amino alcohols. By exploiting the Ru-(S)- i PrPyme catalyst with minimal stereogenicity, a cascade process including dehydrogenation, conjugate addition, and asymmetric reduction was developed. The mild conditions, functional group tolerance, and broad substrate scope (54 examples) demonstrate the synthetic practicality of the catalytic system.
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