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Stereoselective Synthesis of Cyclic Dipeptide Hydroxyalkyl Isosteres via Metalated N,N ‐Dialkylcarbamate 2‐Alkenyl Esters

1991; Wiley; Volume: 30; Issue: 12 Linguagem: Inglês

10.1002/anie.199116901

1521-3773

Rudolf Hanko, Klaus F. Rabe, Robert Dally, Dieter Hoppe,

Chemical Synthesis and Reactions

Potential protease inhibitors are formed stereoselectively by a reaction sequence that begins with the conversion of N-protected α-amino aldehydes with the homoenolate reagent 1. The lactones 2 thus formed may be coupled with α-amino acid amides by a new variation of the Weinreb method in which dialkylaluminum amides are used as ring-opening agents. In this way four diastereomers of the compounds 3 belonging to the Ψ-Phe[CHOHCH] progroup are formed. RCF3CO, CbC(CO)NiPr2, BnPhCH2.