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

doi:10.1021/ol0159221

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 journal › Article › peer-review

151 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 language	English (US)
Pages (from-to)	1973-1976
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	13
DOIs	https://doi.org/10.1021/ol0159221
State	Published - Jun 28 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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 {\AA} molecular sieves. The reactions proceed with moderate yields and at times high enantioselectivty.",

author = "G. Sundararajan and N. Prabagaran and Babu Varghese",

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T1 - First Asymmetric Synthesis of Quinoline Derivatives by Inverse Electron Demand (IED) Diels-Alder Reaction Using Chiral Ti(IV) Complex

AU - Sundararajan, G.

AU - Prabagaran, N.

AU - Varghese, Babu

PY - 2001/6/28

Y1 - 2001/6/28

N2 - (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.

AB - (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.

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U2 - 10.1021/ol0159221

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SP - 1973

EP - 1976

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 13

ER -

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

Abstract

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