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Issue 20, 2005
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Baylis–Hillman reactions of N-tosyl aldimines and aryl aldehydes with 3-methylpenta-3,4-dien-2-one

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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


Submitted
26 Jul 2005
Accepted
19 Aug 2005
First published
09 Sep 2005

Org. Biomol. Chem., 2005,3, 3686-3694
Article type
Paper

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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