Stereocontrolled preparation of cyclohexane amino alcohols utilising a modified Mitsunobu reaction
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 655-661
- https://doi.org/10.1039/p19890000655
Abstract
A method for the introduction of amino groups into aliphatic systems is described. Cyclohex-2-enol reacts with aromatic diacylamines under Mitsunobu reaction conditions to give either N-alkylated or O-alkylated products in a controlled, predictable manner. The product cyclohexenes, with N-bromosuccinimide, give either 1,2- or 1,3-neighbouring group participation leading to 1,2,3-trisubstituted cyclohexanes. The adducts may be used to give a range of 1,2- and 1,3-amino alcohols in a stereocontrolled process.This publication has 2 references indexed in Scilit:
- Synthesis of (L)-daunosamine and related amino sugarsJournal of the Chemical Society, Perkin Transactions 1, 1988
- Ueber eine Darstellungsweise primärer Amine aus den entsprechenden HalogenverbindungenEuropean Journal of Inorganic Chemistry, 1887