Journal of Organic Chemistry p. 4750 - 4754 (1990)
Update date:2022-08-05
Topics:
Solladie-Cavallo, A.
Khiar, N.
Natural (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid is synthesized in 53-55percent yield (referred to (-)-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).
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Doi:10.1016/0022-328X(90)85227-P
(1990)Doi:10.1002/anie.201005373
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(2019)Doi:10.1016/S0040-4020(01)81961-X
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