Carbohydrate as chiral templates

Kunz H., Mueller B., Pfrengle, W., Rueck K., Staehle W. Carbohydrates As Chiral Templates in Stereoselective [4 + 2 Cycloaddition Reactions ACS Symp. Ser. 1992 494 131-146... 

Use of Carbohydrates as Chiral Templates for the Synthesis of the Lipid Portion... 

Kunz. H. and 5ichanzenbach, D., Carbohydrates as chiral templates stereoselective synthesis of (i-aminoacids,Angew. Chem. [nl. Ed. Engl.. 28, 1068, 1989. 

Kunz, H. and Pficngle, W., Carbohydrates as chiral templates stereoselective tandem Man-nich-Michael reanions for tithesis of piperidine alkaloids Angew. Chem. Ini. Ed. EngL. 28, 1067, 1989. 

Staehle, W, Kunz, H, Carbohydrates as chiral templates stereoselective Diels-Alder synthesis with dienes of differing reactivity, Synlett, 260-262, 1991. 

Kunz, H, Sager, W, Schanzenbach, D, Decker, M, Carbohydrates as chiral templates stereoselective Strecker synthesis of D-a-amino nitriles and acids using 0-pivaloylated D-galactosylamine as the auxiliary, Liebigs Ann. Chem., 649-654, 1991. 

Kunz, H, Pfrengle, W, Carbohydrates as chiral templates asymmetric Ugi-synthesis of a-amino acids using galactosylamines as the chiral matrices. Tetrahedron, 44, 5487-5494, 1988. 

Kunz, H, Mohr, J, Carbohydrates as chiral templates reactivity and stereoselectivity of carboxylic ester enolates, 7. Chem. Soc. Chem. Commun., 1315-1317, 1988. 

A stereochemical control of the Ugi reaction can be effected with carbohydrates as chiral templates (e.g. tetrakis(O-pivaloyl)galactosylamine), which gives rise to easily separable amides. From these a variety of non-natural amino acids can be derived after acidic hydrolysis. The Passerini reaction, related to the Ugi rearrangement, gives a-hydroxyamides. A modification of this reaction using titanium tetrachloride gives a-branched amides in high yields via C-metalated imidoyl chlorides (equation 38). 

A review has appeared on the use of carbohydrates as chiral templates in synthesis. ... 

Laschat S, Kunz H. Carbohydrates as chiral templates ster-eoselective synthesis of (R)- and (S)-a-anunophosphonic acid derivatives. Synthesis 1992 (l-2) 90-95. 

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