Examples:

T. Lindel, M. Hochgurtel, J. Org. Chem. 2000, 65, 2806.

A. Tai, F. Matsumura, H. C. Coppel, J. Org. Chem. 1969, 34, 2180.

Furstner, T. Dierkes, Org. Lett. 2000, 2, 2463.

T. Itoh, N. Yamazaki, C. Kibayashi, Org. Lett. 2002, 4, 2469.

 

2.2.6 Reductive Deprotection of Benzyl Group

The benzyl group and cyano group (alkyl nitrile) could be deprotected by dissolved metal in ammonia (Scheme 9).

Scheme 9

 

2.2.7 Bouveault-Blanc reduction

The reduction of carboxylic acid esters to the corresponding alcohols in presence of sodium in ethanol is known as Bouveault-Blanc reduction (Scheme 10). This was one of the important methods for the reduction of carboxylic esters before the discovery of lithium aluminum hydride.

Scheme 10