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Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes by Intramolecular Cleavage of the Rh-C Bond by a Tethered Hydroxy Group

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Title: Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes by Intramolecular Cleavage of the Rh-C Bond by a Tethered Hydroxy Group
Authors: Oonishi, Yoshihiro Browse this author →KAKEN DB
Masusaki, Shuichi Browse this author
Sakamoto, Shunki Browse this author
Sato, Yoshihiro Browse this author →KAKEN DB
Keywords: cyclization
sigma-bond metathesis
Issue Date: 24-Jun-2019
Publisher: Wiley-Blackwell
Journal Title: Angewandte chemie-international edition
Volume: 58
Issue: 26
Start Page: 8736
End Page: 8739
Publisher DOI: 10.1002/anie.201902832
Abstract: Rhodium(I)-catalyzed enantioselective intramolecular cyclization of enynes having a hydroxy group in the tether was investigated, and various cyclic compounds possessing a chiral quaternary carbon center were obtained in high yields with high ees. In this cyclization, a Rh-C(sp(2)) bond in the rhodacyclopentene intermediate, which was formed by enantioselective oxidative cycloaddition of enynes to a chiral rhodium(I) complex, was intramolecularly cleaved by sigma-bond metathesis of a tethered O-H bond in the substrate. Furthermore, it was found that the cyclic compounds were obtained with high ees even when the starting materials having a racemic secondary alcohol moiety were used in this reaction.
Rights: This is the peer reviewed version of the following article: Angewandte chemie-international edition,58(26),8736-8739,(2019), which has been published in final form at . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Type: article (author version)
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 大西 英博

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