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

Molecules

Takamichi Mori¹  Yusuke Akioka¹  Gen Onodera¹ 

[1] id="af1-molecules-19-09288">Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo machi, Nagasaki 852-8521, Jap

关键词: nickel;    homoallylation;    N;    O-acetal;    carbohydrate;    conjugated diene;    triethylborane;    reductive coupling;   

DOI  :  10.3390/molecules19079288

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.