Stereoselective Synthesis of [alpha, alpha][superscript ']-Biprolines

Journal Article · Wed Nov 10 00:00:00 EST 2010 · Org. Lett.

OSTI ID:1008504

Vartak, Ashish P; Johnson, Rodney L ^[1]

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1. Minnesota

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.

• Research Organization: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
• Sponsoring Organization: USDOE
• OSTI ID: 1008504
• Journal Information: Org. Lett., Vol. 7, Issue (1) ; 01, 2005; ISSN 1523-7060
• Country of Publication: United States
• Language: ENGLISH

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AMINO ACIDS
DIMERS
HALIDES
SYNTHESIS
STEREOCHEMISTRY