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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Hydride-transfer domino rearrangement of glycine-containing dioxa-azawurtzitane
Hiroshi Izumi1, Shigeru Futamura
1National Institute of Advanced Industrial Science and Technology, AIST Tsukuba West, 16-1 Onogawa, Tsukuba, Ibaraki 305-8569, Japan. izumi.h@aist.go.jp
Abstract:
The novel synthetic method for dioxa-azawurtzitanes to selectively cap amino groups in amino acids or peptides is described. Mixing the CH(3)CN solution of cis,cis-1,3,5-triformyl-1,3,5-trimethylcyclohexane (2) with the aqueous solution of the equimolar amounts of glycine and NaHCO(3) yields glycine-containing dioxa-azawurtzitane 7-Na. Dioxa-azawurtzitane 7-Na almost quantitatively isomerizes to lactone-imine 9-Na through the hydride-transfer rearrangement in CH(3)CN/H(2)O. Lactone-imine 9-Na also isomerizes to lactam-aldehyde 12-Na in DMSO.
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