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Molecules 2014, 19(7), 9288-9306; https://doi.org/10.3390/molecules19079288

Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane

Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo machi, Nagasaki 852-8521, Japan
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Received: 4 April 2014 / Revised: 13 June 2014 / Accepted: 23 June 2014 / Published: 2 July 2014
(This article belongs to the Special Issue Dynamic Stereochemistry)
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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. View Full-Text
Keywords: nickel; homoallylation; N,O-acetal; carbohydrate; conjugated diene; triethylborane; reductive coupling nickel; homoallylation; N,O-acetal; carbohydrate; conjugated diene; triethylborane; reductive coupling
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Mori, T.; Akioka, Y.; Onodera, G.; Kimura, M. Ni-Catalyzed Homoallylation of Polyhydroxy N,O-Acetals with Conjugated Dienes Promoted by Triethylborane. Molecules 2014, 19, 9288-9306.

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