Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes

Yukimasa Aida, Haruki Sugiyama, Hidehiro Uekusa, Yu Shibata, Ken Tanaka

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

It has been established that a cationic rhodium(I)/axially chiral biaryl bisphosphine complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of α,ω-diynes with electron-rich and unstrained unsymmetrical 1,2-disubstituted alkenes to give chiral multicyclic compounds with good yields and ee values. Interestingly, enantioselectivity highly depends on the structures of α,ω-diynes used presumably due to the presence of two distinct reaction pathways.

Original languageEnglish
Pages (from-to)2672-2675
Number of pages4
JournalOrganic Letters
Volume18
Issue number11
DOIs
Publication statusPublished - 2016 Jun 3
Externally publishedYes

Fingerprint

Diynes
Rhodium
Cycloaddition
Cycloaddition Reaction
cycloaddition
Alkenes
rhodium
alkenes
Enantioselectivity
electrons
Electrons

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes. / Aida, Yukimasa; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken.

In: Organic Letters, Vol. 18, No. 11, 03.06.2016, p. 2672-2675.

Research output: Contribution to journalArticle

Aida, Yukimasa ; Sugiyama, Haruki ; Uekusa, Hidehiro ; Shibata, Yu ; Tanaka, Ken. / Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes. In: Organic Letters. 2016 ; Vol. 18, No. 11. pp. 2672-2675.
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