148312-55-4Relevant articles and documents
Model syntheses of thiazolidine nucleoside analogues
Rassu,Rassu, Gloria,Zanardi,Zanardi, Franca,Cornia,Cornia, Mara,Casiraghi,Casiraghi, Giovanni
, p. 1113 - 1120 (1996)
The syntheses of racemic thiazolidinyl thymine and cytosine derivatives 6a and 6b, and 10a and 10b, prototypes of a novel family of heterosubstituted nucleosides, have been achieved from rhodanine (3) or thiazolidine (7) by a short sequence of steps. The key reaction involved efficient coupling of silylated thymine and cytosine to N-Boc-protected 4- and 5- acetoxythiazolidines, 5 and 9, assisted by tert-butyldimethylsilyl trifluoro- methanesulfonate.
Enantioselective reaction of α-lithiated thiazolidines as new chiral formyl anion equivalents
Wang, Libo,Nakamura, Shuichi,Ito, Yuji,Toru, Takeshi
, p. 3059 - 3072 (2007/10/03)
The reaction of lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine with benzophenone in the presence of (-)-sparteine afforded the products with up to 97% ee and 93% ee, respectively. The reaction with various aromatic and aliphatic aldehydes also afforded the products with high enantioselectivity and moderate diastereoselectivity. Each diastereomer could be converted to optically active diols. Consequently, lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine serve as chiral formyl anion equivalents. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.