Stereoselective synthesis of α,α′-biprolines

Ashish P. Vartak, Victor G. Young, Rodney L. Johnson

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


(Chemical Equation Presented) A means to induce dehydrodimerization of Seebach's oxazolidinone (5), the stereochemical outcome of which is entirely temperature dependent, is described. The resultant dimers 3 and 4 are precursors to (R,R′)-α,α′-biproline (1) and meso-α, α′-biproline (2), respectively. An organohypobromite and an iminium halide are proposed to serve as electrophiles in the reaction with the enolate of 5 to give 3 and 4, respectively.

Original languageEnglish (US)
Pages (from-to)35-38
Number of pages4
JournalOrganic Letters
Issue number1
StatePublished - Jan 6 2005


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