Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes

Takanori Shibata, Hiroshi Kurokawa, Kazumasa Kanda

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

(Chemical Equation Presented) The enantioselective intramolecular [2 + 2 + 2] cycloaddition of various enediynes, where two acetylenic moieties are connected by a trans-olefinic moiety, gave chiral tricyclic cyclohexa-1,3-dienes using Rh-H8-BINAP catalyst. In the case of carbon-atom-tethered enediynes, enantioselectivity was generally good-to-high regardless of the substituents on their alkyne termini. In contrast, with heteroatom-tethered enediynes, appropriate substituents were required to induce the oxidative coupling of alkyne and alkene moieties before that of two alkyne moieties, which would be important for highly enantioselective intramolecular cycloaddition.

Original languageEnglish
Pages (from-to)6521-6525
Number of pages5
JournalJournal of Organic Chemistry
Volume72
Issue number17
DOIs
Publication statusPublished - 2007 Aug 17

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes'. Together they form a unique fingerprint.

Cite this