Stereoselective Synthesis of α,α‘-Biprolines

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...

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Bibliographic Details
Published in:Organic letters 2005-01, Vol.7 (1), p.35-38
Main Authors: Vartak, Ashish P, Young, Victor G, Johnson, Rodney L
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Dimerization
Dipeptides - chemical synthesis
Dipeptides - chemistry
Models, Molecular
Proline - chemical synthesis
Proline - chemistry
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol047958+