✦ LIBER ✦

Synthesis and highly diastereoselective alkylation of chiral N-[(S,S)-3,5-bis(1-methoxyethyl)-1,2,4-triazol-4-yl]arylimines

✍ Scribed by Alan R. Katrizky; Saad R. El-Zemity; Peter Leeming; Chris M. Hartshorn; Peter J. Steel

Book ID: 103977520
Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 472 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(96)00196-6

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✦ Synopsis

Amino-3~5-bis(1-hydroxyethyl)-l,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(1hydroxyethyl)-l,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)-l,2,4-triazol-4-yl]arylimines 4 in very high yield. Subsequent reactions of 4 with Grignard reagents afforded compounds 5 with good to excellent diastereoselectivities in good yield.

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