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

doi:10.1016/S0040-4020(02)00980-8

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal Article › peer-review

84 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 language	English
Pages (from-to)	8299-8305
Number of pages	7
Journal	Tetrahedron
Volume	58
Issue number	41
DOIs	https://doi.org/10.1016/S0040-4020(02)00980-8
Publication status	Published - 7 Oct 2002
Externally published	Yes

Keywords

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

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10.1016/S0040-4020(02)00980-8

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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 = oct,

day = "7",

doi = "10.1016/S0040-4020(02)00980-8",

language = "English",

volume = "58",

pages = "8299--8305",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "41",

}

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 journal › Journal Article › peer-review

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 - https://www.webofscience.com/wos/woscc/full-record/WOS:000178488100018

UR - https://openalex.org/W2005827679

UR - https://www.scopus.com/pages/publications/0037037936

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

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

M3 - Journal Article

SN - 0040-4020

VL - 58

SP - 8299

EP - 8305

JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

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

Keywords

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