Issue 20, 2005
From the journal:

Organic & Biomolecular Chemistry

Baylis–Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one†

Gui-Ling Zhaoa  and  Min Shi*a  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, China
E-mail: Mshi@pub.sioc.ac.cn
Fax: +86 21 64166128

Abstract

The attempted Baylis–Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one gave the corresponding Baylis–Hillman adducts 3 and 6 in moderate to good yields in the presence of DMAP in DMSO, respectively. In the case of the aza-Baylis–Hillman reactions of N-tosyl aldimines with 3-methylpenta-3,4-dien-2-one catalyzed by PBu3, the corresponding aza-Baylis–Hillman derivatives 4 and 5 were formed at the same time.

Graphical abstract: Baylis–Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one

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Article information

DOI
https://doi.org/10.1039/B510572B
Article type
Paper
Submitted
26 Jul 2005
Accepted
19 Aug 2005
First published
09 Sep 2005

Org. Biomol. Chem., 2005,3, 3686-3694

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Baylis–Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one

G. Zhao and M. Shi, Org. Biomol. Chem., 2005, 3, 3686 DOI: 10.1039/B510572B

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