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Enantioselective intramolecular CH insertion route to a key intermediate for the synthesis of trinem antibiotics

✍ Scribed by Masahiro Anada; Shun-ichi Hashimoto

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
280 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new route to the enantiomerically pure azetidin-2-one 3, a key intermediate for the synthesis of trinems, has been developed, incorporating enantioselective intramolecular C-H insertion of ct-methoxycarbonyl-ot-diazoacetamide catalyzed by chiral Rh(II) complexes and diastereoselective arene hydrogenation as the key steps. The use of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] as a catalyst produced the desired azetidinone in 84% ee, whereas catalysis with dirhodium(II) tetrakis[N-phthaloyl-(S)-alaninate] afforded its enantiomer in 84% ee.

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