Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C 3 ‐Chirogenic Center | Zendy

Liu Chong | Zendy; Yuan Jing | Zendy; Zhang Zhenfeng | Zendy; Gridnev Ilya D. | Zendy; Zhang Wanbin | Zendy

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Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C 3 ‐Chirogenic Center

Author(s) -

Liu Chong,

Yuan Jing,

Zhang Zhenfeng,

Gridnev Ilya D.,

Zhang Wanbin

Publication year - 2021

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.202017190

Subject(s) - hydroacylation , alkene , isomerization , intramolecular force , enantioselective synthesis , chemistry , catalysis , stereochemistry , organic chemistry , aldehyde

A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five‐membered rhodacycle intermediate, 3‐enals were converted to C 3 ‐ or C 3 ,C 5 ‐chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.

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