Applications of Baylis-Hillman coupling products: A remarkable reversal of stereochemistry from esters to nitriles: A simple synthesis of (2E)-2-methylalk-2-en-1-ols and (2Z)-2-methylalk-2-enenitriles

Abstract

Reaction of methyl 3-acetoxy-2-methylenealkanoates with the reducing agent, lithium aluminium hydride (LAH): ethanol (1 : 1), provides (2E)-2-methylalk-2- en-1-ols, whereas, reaction of 3-acetoxy-2-methylenealkanenitriles with the same reagent provides (2Z)-2-methylalk-2-enenitriles in high yields.