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Enantioselective Synthesis of ( R )‐ N ‐Boc‐1‐amino‐2‐arylcyclopropene‐1‐carboxylic Acid Methyl Ester
Author(s) -
Schöllkopf Ulrich,
Hupfeld Bernd,
Küper Stephan,
Egert Ernst,
Dyrbusch Michael
Publication year - 1988
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.198804331
Subject(s) - enantioselective synthesis , ether , carbene , chemistry , stereochemistry , molecule , enzyme , carboxylic acid , organic chemistry , catalysis
The addition of a bislactim ether carbene to an arylethyne is the key step in the synthesis of the title compounds 1 . cyclo ‐( L ‐Val‐Gly) 2 , used as lactim ether, furnishes the target molecules ( R )‐ 1 in almost enantiomerically pure form, while ent ‐ 2 correspondingly furnishes the ( S )‐isomers. Compounds of the type 1 should be very effective suicide‐inhibitors for pyridoxalphosphate‐dependent enzymes (RH, CH 3 , Cl).