A New and Convenient Method for the Synthesis of Dehydroamino Acids Starting from Ethyl N-Boc- and N-Z-α-Tosylglycinates and Various Nitro Compounds
Author(s) -
Tanemasa Nagano,
Hideki Kinoshita
Publication year - 2000
Publication title -
bulletin of the chemical society of japan
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.145
H-Index - 99
eISSN - 1348-0634
pISSN - 0009-2673
DOI - 10.1246/bcsj.73.1605
Subject(s) - chemistry , formic acid , glyoxylate cycle , carbamate , stereochemistry , ethyl carbamate , organic chemistry , medicinal chemistry , enzyme , food science , wine
Ethyl N-Boc- and N-Z-α-tosylglycinates, which were readily available from t-butyl or benzyl carbamate, ethyl glyoxylate, and sodium p-toluenesulfinate in formic acid, were reacted with a variety of nitro compounds in the presence of a base to afford the corresponding α,β-didehydroamino acid derivatives in good yields. Eventually, it was found that the (Z)-isomer was predominantly formed in the present method
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