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

Oonishi Yoshihiro | Zendy; Masusaki Shuichi | Zendy; Sakamoto Shunki | Zendy; Sato Yoshihiro | Zendy

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

Author(s) -

Oonishi Yoshihiro,

Masusaki Shuichi,

Sakamoto Shunki,

Sato Yoshihiro

Publication year - 2019

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201902832

Subject(s) - enantioselective synthesis , rhodium , chemistry , intramolecular force , moiety , bond cleavage , cycloaddition , stereochemistry , metathesis , catalysis , medicinal chemistry , organic chemistry , polymerization , polymer

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 ee s. 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 σ‐bond metathesis of a tethered O−H bond in the substrate. Furthermore, it was found that the cyclic compounds were obtained with high ee s even when the starting materials having a racemic secondary alcohol moiety were used in this reaction.

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