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. 2014 Jul 2;19(7):9288-306.
doi: 10.3390/molecules19079288.

Ni-catalyzed homoallylation of polyhydroxy n,o-acetals with conjugated dienes promoted by triethylborane

Takamichi Mori  1 , Yusuke Akioka  1 , Gen Onodera  1 , Masanari Kimura  2
Affiliations

Ni-catalyzed homoallylation of polyhydroxy n,o-acetals with conjugated dienes promoted by triethylborane

Takamichi Mori et al. Molecules. .

Abstract

In the presence of Ni-catalyst and triethylborane, N,O-acetals prepared from glycolaldehyde and glyceraldehyde with primary amines in situ underwent homoallylation with conjugated dienes to provide 2-amino-5-hexenols in high regio- and stereoselectivity. Under similar reaction conditions, N,O-acetals from carbohydrates with primary amines provided the corresponding polyhydroxy-bishomoallylamines in good to reasonable yields.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Equilibrium between cyclic N,O-acetal and ω-hydroxyamine.
See this image and copyright information in PMC

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