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J Org Chem. 2017 Dec 1;82(23):12050-12058. doi: 10.1021/acs.joc.7b01751. Epub 2017 Oct 30.

Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994.

Author information

1
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , Daejeon 34141, Korea.
2
Department of Chemistry, University of Toronto , Toronto M5S 3H6, Canada.

Abstract

The stereoselective synthesis of mixed alkyl-aryl vicinal diamines was demonstrated by the use of 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethene (hpen). A sequential addition of aryl and alkyl aldehyde to hpen gave a fused imidazolidine-dihydro-1,3-oxazine ring stereoselectively, which undergoes the diaza-Cope rearrangement to provide mixed vicinal diimines at elevated temperature in good yields and excellent stereoselectivity. We also showed that (+)-CP-99,994 can be readily prepared by the diaza-Cope rearrangement in overall 42% yield.

PMID:
29027460
DOI:
10.1021/acs.joc.7b01751

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