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Approach to chiral vicinal diacylamines by Bamberger ring cleavage of substituted imidazoles (1990)

Altman, Janina ; Grinberg, Mircea ; Wilchek, Meir

Weinheim : Wiley-Blackwell

Liebigs Annalen 1990 (1990), S. 339-343

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ISSN: 0170-2041

Keywords: Chiral vicinal diacylamines ; Bamberger ring cleavage ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Ring cleavage of ethyl 3-[4(5)-imidazolyl]propanoate (1) with (-)-menthyl chloroformate introduces chiral carbamate substituents on the double bond which, upon hydrogenation, induces preferred formation of ethyl (4S)-4,5-bis[(-)-menthyl-oxycarbonylamino]pentanoate (5) (5:1 ratio of diastereomers). The ring cleavage benzoylation product of (S)-histidine methyl ester, with a chiral center in the side chain, gives rise to (2S,4R)/(2S,4S)-2,4,5-tribenzamidopentanoates (13, 14), in 2:1 ratio upon hydrogenation.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199019900164

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