Synthetic Communications®

Facile and Chemoselective Cleavage of Allyl Carboxylic Ester Utilizing NaBH4 in DMSO

BV Pawar, PD Lokhande

Index: Pawar, Bharati V.; Lokhande, Pradeep D. Synthetic Communications, 2009 , vol. 39, # 14 p. 2445 - 2453

Full Text: HTML

Citation Number: 0

Abstract

Abstract A new method for deprotection of allyl carboxylic ester has been observed by using the inexpensive reagent sodium borohydride in dimethyl sulfoxide (DMSO). Aliphatic and aromatic allyl carboxylic ester undergo deprotection smoothly. The allyl ester group can selectively deprotect better than phenol.

~90%

~92%

~85%

~88%

~78%

~82%

~87%

An in-depth study of the biotransformation of nitriles into ...

[Meth-Cohn, Otto; Wang, Mei-Xiang Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 8 p. 1099 - 1104]

A mild oxidation of aromatic amines

[Webb, Kevin S.; Seneviratne, Viran Tetrahedron Letters, 1995 , vol. 36, # 14 p. 2377 - 2378]

An efficient method for one-carbon elongation of aryl aldehy...

[Huh, Dal Ho; Jeong, Ji Sang; Lee, Hee Bong; Ryu, Hoejin; Kim, Young Gyu Tetrahedron, 2002 , vol. 58, # 50 p. 9925 - 9932]

Electrophilic aromatic substitution with N-methoxy-N-acylnit...

[Journal of Organic Chemistry, , vol. 54, # 14 p. 3394 - 3403]

Hydrolysis of esters and amides in strongly basic solution. ...

[Journal of Organic Chemistry, , vol. 46, # 6 p. 1186 - 1191]