Concurrent induction of two chiral centers from symmetrical 3, 4-disubstituted and 3,3,4-trisubstituted 4-pentenals using Rh-catalyzed asymmetric cyclizations

@article{Tanaka2000ConcurrentIO,
  title={Concurrent induction of two chiral centers from symmetrical 3, 4-disubstituted and 3,3,4-trisubstituted 4-pentenals using Rh-catalyzed asymmetric cyclizations},
  author={Tanaka and Imai and Fujio and Sakamoto and Takahashi and Eto-Kato and Wu and Funakoshi and Sakai and Suemune},
  journal={The Journal of organic chemistry},
  year={2000},
  volume={65 18},
  pages={
          5806-16
        }
}
  • Tanaka, Imai, +7 authors Suemune
  • Published 2000
  • Chemistry, Medicine
  • The Journal of organic chemistry
Asymmetric cyclization of symmetrical 3,4-disubstituted and 3,3, 4-trisubstituted 4-pentenals was studied using Rh-complexes with chiral ligands. The cyclization of symmetrical 4-pentenals 4a,b by a neutral Rh[(R)-BINAP]Cl afforded cis-3,4-disubstituted (4R)-cyclopentanones 9a,b of >95% ee in 25-31% yields; on the other hand, the cyclization of 4a-c by a cationic Rh[(R)-BINAP]ClO(4) afforded trans-3,4-disubstituted (4S)-cyclopentanones 10a-c of >95% ee in 70-81% yields. All stereoisomers could… Expand
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