Abstract
(S,S)-4-Amino-3,5-bis(1-hydroxyethyl)-1,2,4-triazole
2 (SAT) (from (S)-lactic acid and hydrazine hydrate) reacted with substituted benzaldehydes
6 to afford N-[(S,S)-3,5-bis(1-hydroxyethyl)-1,2,4-triazol-4-yl]arylimines
3 in excellent yield. Protection of the hydroxyl groups in compounds
3 was accomplished using methyl tosylate under mild conditions to give N-[(S,S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines
4 in very high yield. Subsequent reactions of
4 with Grignard reagents afforded compounds
4 with good to excellent diastereoselectivities in good yield.
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