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Construction of Optically Pure Tryptophans from Serine Derived Aziridine-2-carboxylates by Kazuo Sato; Alan P. Kozikowski is a Chemistry article available to read on EtoBox.

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The possibility of preparing optically pure tryptophan derivatives from various substituted indoles and (2R)-or (2S)-Z-aziridinecarboxylates has been examined. Zinc triflate was found to be the only Lewis acid capable of bringing about this reaction in moderate yields. During efforts aimed at the synthesis of various analogues of lyngbyatoxin Al for use in studies pertaining to the modulation of protein kinase C activity,:! we became interested in the possibility of procuring optically pure tryptophan derivatives directly from indoles by reaction with optically pure azlridines (Equation 1). ## Cbz -'?ry (Equation 1) While reports of related reactions can be found in the literature,3 such examples are few in number, and no examples pertaining to the use of (optically pure) aziridinecarboxylates have been published.

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Author

Kazuo Sato; Alan P. Kozikowski

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1989

Language

EN

Field

Chemistry (Physical Sciences)