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The Journal of Organic Chemistry

Synthesis of (2S, 3R)-3-amino-2-hydroxy-5-methylhexanoic acid: bridging effect of potassium fluoride

A Solladié-Cavallo, N Khiar

文献索引:Solladie-Cavallo, A.; Khiar, N. Journal of Organic Chemistry, 1990 ,  vol. 55,  # 15  p. 4750 - 4754

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被引用次数: 21

摘要

Natural (2S, 3R)-3-amino-2-hydroxy-5-methylhexanoic acid is synthesized in 53-5570 yield (referred to (-1-8-phenylmenthol used as chiral auxiliary) by condensation of 1-nitro-3- methylbutane on (-)-8-phenylmenthol glyoxylate hydrate using KF as a mild base. With a large excess of KF in THF it has been possible to increase the diastereoselectivity of the nitro aldol condensation (up to I/II/III/IV= 77/13/10/0). ua