Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction

Kyoung Hoon Kim; Seil Lee; Dae Woong Lee; Dong Hyun Ko; Deok Chan Ha

doi:10.1016/j.tetlet.2005.07.025

Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction

Kyoung Hoon Kim, Seil Lee, Dae Woong Lee, Dong Hyun Ko, Deok Chan Ha

College of Science

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

55 Citations (Scopus)

Abstract

Bisammonium salts of mono-N-alkylated chiral 1,2-diamino-1,2-diphenylethane (DPEN) were employed in the catalytic and asymmetric Diels-Alder reaction between cyclopentadiene and crotonaldehyde. The N-3-pentyl diamine·2HCl catalyst shows high endo/exo selectivity and endo-enantioselectivity for the cycloaddition, and this organocatalysis is the first example of the use of a chiral 1,2-diamine to generate an imine intermediate which is activated by an internal ammonium Brønsted acid for the cycloaddition in a wet solvent.

Original language	English
Pages (from-to)	5991-5994
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2005.07.025
Publication status	Published - 2005 Sept 5

Bibliographical note

Funding Information:
This work was financially supported by the Center for Molecular Design and Synthesis (CMDS) at KAIST.

Keywords

Aldehydes
Ammonium salts
Asymmetric Diels-Alder
Cyclopentadiene
Organocatalysis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.07.025

Cite this

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title = "Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction",

abstract = "Bisammonium salts of mono-N-alkylated chiral 1,2-diamino-1,2-diphenylethane (DPEN) were employed in the catalytic and asymmetric Diels-Alder reaction between cyclopentadiene and crotonaldehyde. The N-3-pentyl diamine·2HCl catalyst shows high endo/exo selectivity and endo-enantioselectivity for the cycloaddition, and this organocatalysis is the first example of the use of a chiral 1,2-diamine to generate an imine intermediate which is activated by an internal ammonium Br{\o}nsted acid for the cycloaddition in a wet solvent.",

keywords = "Aldehydes, Ammonium salts, Asymmetric Diels-Alder, Cyclopentadiene, Organocatalysis",

author = "Kim, {Kyoung Hoon} and Seil Lee and Lee, {Dae Woong} and Ko, {Dong Hyun} and Ha, {Deok Chan}",

note = "Funding Information: This work was financially supported by the Center for Molecular Design and Synthesis (CMDS) at KAIST. ",

year = "2005",

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doi = "10.1016/j.tetlet.2005.07.025",

language = "English",

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T1 - Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction

AU - Kim, Kyoung Hoon

AU - Lee, Seil

AU - Lee, Dae Woong

AU - Ko, Dong Hyun

AU - Ha, Deok Chan

N1 - Funding Information: This work was financially supported by the Center for Molecular Design and Synthesis (CMDS) at KAIST.

PY - 2005/9/5

Y1 - 2005/9/5

N2 - Bisammonium salts of mono-N-alkylated chiral 1,2-diamino-1,2-diphenylethane (DPEN) were employed in the catalytic and asymmetric Diels-Alder reaction between cyclopentadiene and crotonaldehyde. The N-3-pentyl diamine·2HCl catalyst shows high endo/exo selectivity and endo-enantioselectivity for the cycloaddition, and this organocatalysis is the first example of the use of a chiral 1,2-diamine to generate an imine intermediate which is activated by an internal ammonium Brønsted acid for the cycloaddition in a wet solvent.

AB - Bisammonium salts of mono-N-alkylated chiral 1,2-diamino-1,2-diphenylethane (DPEN) were employed in the catalytic and asymmetric Diels-Alder reaction between cyclopentadiene and crotonaldehyde. The N-3-pentyl diamine·2HCl catalyst shows high endo/exo selectivity and endo-enantioselectivity for the cycloaddition, and this organocatalysis is the first example of the use of a chiral 1,2-diamine to generate an imine intermediate which is activated by an internal ammonium Brønsted acid for the cycloaddition in a wet solvent.

KW - Aldehydes

KW - Ammonium salts

KW - Asymmetric Diels-Alder

KW - Cyclopentadiene

KW - Organocatalysis

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U2 - 10.1016/j.tetlet.2005.07.025

DO - 10.1016/j.tetlet.2005.07.025

M3 - Article

AN - SCOPUS:23344442773

SN - 0040-4039

VL - 46

SP - 5991

EP - 5994

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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