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Positional isomers of naturally occurring peptide subunits were synthesized via highly diastereoselective reduction of tert-butylsulfinyl ketimines as a key reaction. While NaBH 4 reduction of ketimines derived from 2-thiazolyl ketones afforded the (R S ,R)-isomer with moderate diastereoselectivity, L-Selectride ® reduction afforded the (R S ,S)-isomer as the sole product. In contrast, ketimines derived from tert-butyl 2-thiazolyl ketone afforded the (R S ,R)-isomer with low diastereoselectivity by both NaBH 4 and L-Selectride ® reduction. Stereochemistry of the reaction was discussed based on calculation of the conformational energies for ketimines.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Highly Diastereoselective Synthesis of 2-(1-&lt;i&gt;N&lt;/i&gt;-Boc-aminoalkyl)thiazole-5-carboxylates by Reduction of &lt;i&gt;tert&lt;/i&gt;-Butylsulfinyl Ketimines