http://dx.doi.org/10.1002/adsc.201000438">
 

Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Second generation CaSH (camphor sulfonyl hydrazine) organocatalysis. asymmetric diels–alder reactions and isolation of the catalytic intermediate

Language

English

Abstract

In one step, the well known chiral auxiliary, Oppolzer's camphor sultam, is turned into the new generation camphor sulfonyl hydrazine (CaSH II) organocatalyst. With the primary hydrazine functionality external to the tricyclic structure, CaSH II is active towards ketone substrates in asymmetric Diels-Alder reactions. The iminium intermediate of the catalytic cycle was isolated. When it was put back into the solution reaction system, the same level of yield and stereoselectivity was observed. Based on these observations, we argue that organocatlyst is actually an in situ chiral auxiliary. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

Asymmetric diels-alder reaction, Camphor sulfonyl hydrazine, CaSH, Hydrazines, Organocatalysis

Publication Date

2010

Source Publication Title

Advanced Synthesis and Catalysis

Volume

352

Issue

13

Start Page

2142

End Page

2146

Publisher

Wiley-VCH Verlag

ISSN (print)

16154150

ISSN (electronic)

16154169

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