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Asymmetric synthesis of (2R,5R)-2,5-diaminohexan-1,6-dioic acid

✍ Scribed by Steven D Bull; Alexander N Chernega; Stephen G Davies; William O Moss; Richard M Parkin

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 528 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00492-x

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✦ Synopsis

Sch611kopf's auxiliary 16 was added to bis-lactim iodide 21 to give 1,2-bis[(3S,6R)-3,6dihydro-2,5-dimethoxy-3-isopropylpyrazin-6-yl]ethane 22 in 50% d,e. Dimer 22 was separated from its diastereoisomer 23 and deprotected using 6M HCI to afford homochiral (2R,5R)-2,5-diaminohexan-1,6dioic acid 24.

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