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Stereoselective synthesis of cyclopropane-1,2-bis(glycine) derivatives

✍ Scribed by Siren Neset; Håkon Hope; Kjell Undheim

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
756 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Conformationally constrained bis(glycines) as trans derivatives of cyclopropane have been prepared in stereoselective syntheses. (S)-4-Benzyl-2-oxazolidinone was used as a chiral auxiliary, trisyl azide was the electrophilic source of amine nitrogen. Four stereogenic centers were created. A related cis-cyclopropane derivative suffered ring closure with formation of a bicyclo[3.1.0]hex-3-one derivative.

X-ray data for the latter and for (1S,2S)-1,2-bis{(lS)-azido-2-oxo-2[(4S)-benzyl-2-oxo-3-oxazolidinyl]ethyl }cyclopropane are presented.

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