Next Article in Journal
N-Alkyl Carbazole Derivatives as New Tools for Alzheimer’s Disease: Preliminary Studies
Next Article in Special Issue
Homoconjugation vs. Exciton Coupling in Chiral α,β-Unsaturated Bicyclo[3.3.1]nonane Dinitrile and Carboxylic Acids
Previous Article in Journal
Chitosan-Coated Magnetic Nanoparticles Prepared in One-Step by Precipitation in a High-Aqueous Phase Content Reverse Microemulsion
Previous Article in Special Issue
Chiroptical Properties and the Racemization of Pyrene and Tetrathiafulvalene-Substituted Allene: Substitution and Solvent Effects on Racemization in Tetrathiafulvalenylallene
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(7), 9288-9306; doi: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
*
Author to whom correspondence should be addressed.
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)
View Full-Text   |   Download PDF [299 KB, uploaded 2 July 2014]   |  

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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top