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

Basavaiah, Deevi ; Sarma, Pakala K. S. (1992) 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 Journal of the Chemical Society - Series Chemical Communications, 1992 (13). pp. 955-957. ISSN 0022-4936

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1992...

Related URL: http://dx.doi.org/10.1039/C39920000955

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.

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