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Literature DB >> 15624971

Stereoselective synthesis of alpha,alpha'-biprolines.

Ashish P Vartak¹, Victor G Young, Rodney L Johnson.

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.

Entities: Chemical

Mesh：

Substances：
Dipeptides
Proline

Year: 2005 PMID： 15624971 PMCID： PMC1388272 DOI： 10.1021/ol047958+

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

3 in total

1. Highly Stereocontrolled Cyclopropanation by the 1,3-Elimination of a Bis(tributylstannyl)propanol Derivative.

Authors: Naohiro Isono; Miwako Mori
Journal: J Org Chem Date: 1996-11-01 Impact factor: 4.354

2. Asymmetric Oxidative Dimerization of the Enolates of N-[Bis(methylthio)methylene]- and N-(Diphenylmethylene)glycine Esters.

Authors: Carlos Alvarez-Ibarra; Aurelio G. Csákÿ; Belén Colmenero; M. Luz Quiroga
Journal: J Org Chem Date: 1997-04-18 Impact factor: 4.354

Stereoselective synthesis of alpha,alpha'-biprolines.

1. Highly Stereocontrolled Cyclopropanation by the 1,3-Elimination of a Bis(tributylstannyl)propanol Derivative.

2. Asymmetric Oxidative Dimerization of the Enolates of N-[Bis(methylthio)methylene]- and N-(Diphenylmethylene)glycine Esters.

3. Asymmetric Michael addition of alpha-hydroxyketones to nitroolefins catalyzed by chiral diamine.

1. Concerted synthesis of a spirobicyclic type-VI beta-turn mimic of Pro-Pro-Pro-NH2.

2. Stereoselective Synthesis of Quaternary Proline Analogues.

3. Development of peptidomimetic ligands of Pro-Leu-Gly-NH(2) as allosteric modulators of the dopamine D(2) receptor.