First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex.
[reaction: see text] (R,R)-3-Aza-3-benzyl-1,5-dihydroxy-1,5-diphenylpentane (1) ligated Ti(IV) complex (1-TiCl(2)) 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 A molecular sieves. The reactions proceed with moderate yields and at times high enantioselectivty.
Sundararajan
G
G
Department of Chemistry and Regional Sophisticated Instrumentation Centre, Indian Institute of Technology Madras, India 600 036. gsundar@iitm.ac.in
Narayanasamy
Prabagaran
P
Department of Chemistry and Regional Sophisticated Instrumentation Centre, Indian Institute of Technology Madras, India 600 036. gsundar@iitm.ac.in
Varghese
B
B
Department of Chemistry and Regional Sophisticated Instrumentation Centre, Indian Institute of Technology Madras, India 600 036. gsundar@iitm.ac.in
D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D014961:X-Ray Diffraction
D011804:Quinolines