The base-catalyzed hydroazidation of alpha'-amino alpha,beta-unsaturated ketones with in situ generated hydrazoic acid was found to proceed with highstereoselectivity in favor of the syn product. The stereoselectivity is controlled by the configuration of the enone and syn/anti ratios up to 7:1were obtained with secondary and tertiary amines at low temperature. By this route the diamino alcohol core of HIV-PR inhibitors ritonavir andlopinavir was synthesized in 37% yield from phenylalanine.

Synthesis of a val-pro diaminodiol dipeptide isostere by epoxyamine cyclization

BENEDETTI, FABIO;BERTI, FEDERICO;DINON, FRANCESCA;NARDIN, GIORGIO;NORBEDO, STEFANO
2004-01-01

Abstract

The base-catalyzed hydroazidation of alpha'-amino alpha,beta-unsaturated ketones with in situ generated hydrazoic acid was found to proceed with highstereoselectivity in favor of the syn product. The stereoselectivity is controlled by the configuration of the enone and syn/anti ratios up to 7:1were obtained with secondary and tertiary amines at low temperature. By this route the diamino alcohol core of HIV-PR inhibitors ritonavir andlopinavir was synthesized in 37% yield from phenylalanine.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/1690765
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