166734-67-4Relevant academic research and scientific papers
The Influence of Protecting Group Character on the Diastereoselectivity of Thiazolidine Ring Formation from Amino Aldehydes and Cysteine
Wyslouch, Aleksandra,Lisowski, Marek,Siemion, Ignacy Z.
, p. 117 - 130 (2007/10/02)
A series of 2-(1'-aminoalkyl)-thiazolidine-4-carboxylic acid derivatives was synthesized by condensation of (R)- or (S)-Cys with the amino aldehydes obtained from N-Boc-protected (S)-Ile, (S)-Leu, O-Bzl-(S)-Tyr, (S)- and (R)-Phe, and N-Z-(S)-Phe, N-Pht-(S)-Phe and N-(Pht)-(R)-Phe. All compounds were studied by 1H NMR and CD. The 2D NOESY experiments were carried out to determine the configuration of the newly formed stereogenic centre in position 2 of the thiazolidine ring. It was found that the configuration on the thiazolidine C2 atom is R or S when N-Boc- and N-Z-(S)-amino aldehydes or N-Boc- and N-Z-(R)-amino aldehydes are used in the reaction, respectively. The situation is opposite in the case of N-Pht-Phe derived amino aldehydes. The relation between the C2 atom configuration and the shape of CD spectra is discussed. Key words: 2-(1'-aminoalkyl)-thiazolidine-4-carboxylic acids, amino aldehydes, cysteine, stereoselectivity, absolute configuration, NMR, CD.
