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Stereoselective Synthesis of Cyclic Dipeptide Hydroxyalkyl Isosteres via Metalated N,N ‐Dialkylcarbamate 2‐Alkenyl Esters
Author(s) -
Hanko Rudolf,
Rabe Klaus,
Dally Robert,
Hoppe Dieter
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199116901
Subject(s) - dipeptide , diastereomer , stereoselectivity , chemistry , reagent , stereochemistry , ring (chemistry) , amino acid , protease , enzyme , organic chemistry , biochemistry , catalysis
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. RCF 3 CO, CbC(CO)N i Pr 2 , BnPhCH 2 .