The first catalytic enantioselective Diels-Alder reactions of 1,2-dihydropyridine: Efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes

Norito Takenaka, Yong Huang, Viresh H. Rawal

Research output: Contribution to journalArticle

77 Citations (Scopus)

Abstract

We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels-Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels-Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89-99%) and with moderate to good enantioselectivities (79-85%).

Original languageEnglish (US)
Pages (from-to)8299-8305
Number of pages7
JournalTetrahedron
Volume58
Issue number41
DOIs
StatePublished - Oct 7 2002
Externally publishedYes

Fingerprint

Azabicyclo Compounds
Schiff Bases
Enantioselectivity
Cycloaddition Reaction
Catalysts
1,4-dihydropyridine
disalicylaldehyde ethylenediamine

Keywords

  • 2-azabicyclo[2.2.2]octane
  • Alkaloids
  • Asymmetric catalysis
  • Diels-Alder reaction
  • Enantioselective

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The first catalytic enantioselective Diels-Alder reactions of 1,2-dihydropyridine : Efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes. / Takenaka, Norito; Huang, Yong; Rawal, Viresh H.

In: Tetrahedron, Vol. 58, No. 41, 07.10.2002, p. 8299-8305.

Research output: Contribution to journalArticle

@article{95918194c1e54ef4b639b24fb983e900,
title = "The first catalytic enantioselective Diels-Alder reactions of 1,2-dihydropyridine: Efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes",
abstract = "We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels-Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels-Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89-99{\%}) and with moderate to good enantioselectivities (79-85{\%}).",
keywords = "2-azabicyclo[2.2.2]octane, Alkaloids, Asymmetric catalysis, Diels-Alder reaction, Enantioselective",
author = "Norito Takenaka and Yong Huang and Rawal, {Viresh H.}",
year = "2002",
month = "10",
day = "7",
doi = "10.1016/S0040-4020(02)00980-8",
language = "English (US)",
volume = "58",
pages = "8299--8305",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "41",

}

TY - JOUR

T1 - The first catalytic enantioselective Diels-Alder reactions of 1,2-dihydropyridine

T2 - Efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes

AU - Takenaka, Norito

AU - Huang, Yong

AU - Rawal, Viresh H.

PY - 2002/10/7

Y1 - 2002/10/7

N2 - We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels-Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels-Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89-99%) and with moderate to good enantioselectivities (79-85%).

AB - We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels-Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels-Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89-99%) and with moderate to good enantioselectivities (79-85%).

KW - 2-azabicyclo[2.2.2]octane

KW - Alkaloids

KW - Asymmetric catalysis

KW - Diels-Alder reaction

KW - Enantioselective

UR - http://www.scopus.com/inward/record.url?scp=0037037936&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037037936&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(02)00980-8

DO - 10.1016/S0040-4020(02)00980-8

M3 - Article

AN - SCOPUS:0037037936

VL - 58

SP - 8299

EP - 8305

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 41

ER -