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Cover Picture: Rhodium(I)‐Catalyzed Enantioselective Cyclization of Enynes by Intramolecular Cleavage of the Rh−C Bond by a Tethered Hydroxy Group (Angew. Chem. Int. Ed. 26/2019)
Author(s) -
Oonishi Yoshihiro,
Masusaki Shuichi,
Sakamoto Shunki,
Sato Yoshihiro
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201905962
Subject(s) - chemistry , rhodium , bond cleavage , enantioselective synthesis , hydride , intramolecular force , medicinal chemistry , catalysis , cleavage (geology) , stereochemistry , organic chemistry , materials science , fracture (geology) , hydrogen , composite material
A chiral quaternary carbon center at the ring junction can be prepared by Rh I ‐catalyzed cyclization of enynes, as described by Y. Oonishi, Y. Sato et al. in their Communication on page 8736 ff. It was revealed that the cyclization proceeds through a novel reaction pathway. The cleavage of the Rh−C(sp 2 ) bond of the chiral rhodacycle by an O−H bond in the tether occurs, then β‐hydride elimination from the resultant oxarhodacycle, followed by reductive elimination to give cyclic compounds with a chiral quaternary carbon center in high yields and with high ee values.