Article ID Journal Published Year Pages File Type
1348234 Tetrahedron: Asymmetry 2006 6 Pages PDF
Abstract

Depending on the experimental conditions, aspartic and glutamic anhydrides can be opened regioselectively with Grignard reagents, thus giving access to different isomers of chiral amino-ketoesters.

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(4S)-Methyl 4-(benzyloxycarbonylamino)-5-oxo-5-phenylpentanoateC20H21NO5[α]D20=+29.0 (c 1, CH2Cl2)

(4S)-Methyl 4-(benzyloxycarbonylamino)-5-oxononanoateC18H25NO5[α]D20=+24.4 (c 1, CH2Cl2)

(4S)-Methyl 4-(benzyloxycarbonylamino)-5-(3-methoxyphenyl)-5-oxopentanoateC21H23NO6[α]D20=+23.6 (c 1, CH2Cl2)

(4S)-Methyl 4-(benzyloxycarbonylamino)-5-oxoundecanoateC20H29NO5[α]D20=+13.1 (c 1, CH2Cl2)

(S)-tert-Butyl 2-(benzyloxycarbonylamino)-5-oxo-5-phenylpentanoateC18H25NO5[α]D20=+6.8 (c 0.45, CHCl3)

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
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