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Stereoselective synthesis of alpha,alpha'-biprolines.

ABSTRACT: 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)-alpha,alpha'-biproline (1) and meso-alpha,alpha'-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.

SUBMITTER: Vartak AP

PROVIDER: S-EPMC1388272 | biostudies-literature | 2005 Jan

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of alpha,alpha'-biprolines.

Vartak Ashish P AP Young Victor G VG Johnson Rodney L RL

Organic letters 20050101 1

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)-alpha,alpha'-biproline (1) and meso-alpha,alpha'-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. ...[more]

PMID: 15624971

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