First Asymmetric Synthesis of Quinoline Derivatives by Inverse Electron Demand (IED) Diels-Alder Reaction Using Chiral Ti(IV) Complex

G. Sundararajan, N. Prabagaran, Babu Varghese

Research output: Contribution to journalArticle

146 Scopus citations

Abstract

(matrix presented) R1, R2 = (-OCH2CH2-), (-OCH2CH2CH2-), (-CH=CH-CH2-), (-OCH2CH3, H) (R,R)-3-Aza-3-benzyl-1,5-dihydroxy-1,5-diphenylpentane (1) ligated Ti(IV) complex (1-TiCl2) is used as a chiral Lewis acid catalyst for promoting asymmetric IED Diels-Alder reaction between electron-rich dienophiles and electron-poor dienes. Here we introduce a facile route for the synthesis of asymmetric tetrahydroquinoline derivatives using the above-mentioned chiral catalyst reagent in the presence of 4 Å molecular sieves. The reactions proceed with moderate yields and at times high enantioselectivty.

Original languageEnglish (US)
Pages (from-to)1973-1976
Number of pages4
JournalOrganic Letters
Volume3
Issue number13
DOIs
StatePublished - Jun 28 2001

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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