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DOI: 10.1055/s-2006-926337
Alternate, Easy and Practical Synthesis of Allylamines from Acetyl Derivatives of Baylis-Hillman Adducts Using Methanolic Ammonia [1]
Publication History
Publication Date:
07 February 2006 (online)
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Abstract
A methanolic ammonia-mediated alternate, easy and practical stereoselective synthesis of allylamines from the acetyl derivatives of Baylis-Hillman adducts is described.
Key words
Baylis-Hillman - allylamine - methanolic ammonia - stereoselective
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References
CDRI Communication No. 6786.
6Singh V., Pathak R., Kanojiya S., Batra S.; Synlett; 2005, 2465.
9During extensive exploratory studies on the Baylis-Hillman derivatives we have observed that reaction between acetyl derivatives of Baylis-Hillman adducts and primary amines (ca 1-1.5-fold) always lead to tertiary amines (Figure [1] ) as the major product. However, the formation of such an amine can be reduced by using excess amine (ca. 4-fold) and adding acetyl derivative slowly under cold conditions.
Figure 1 Structure of tertiary amines formed in the reaction of primary amines with Baylis-Hillman adducts.
Several experiments using ESI mass spectrometry technique in the presence of NH4OH and/or NH4OAc (5-6 mM) were carried out to establish the exact molecular weight of products.