87363-79-9Relevant articles and documents
Novel stereospecific dehydration of β-hydroxy-α-amino acids using Martin's sulfurane
Yokokawa, Fumiaki,Shioiri, Takayuki
, p. 8679 - 8682 (2002)
The stereospecific dehydration of threo-N-acyl-β-hydroxy-α-amino acid derivatives was performed using Martin's sulfurane to give (Z)-α,β-dehydroamino acids, while erythro-N-acyl-β-hydroxy-α-amino acid amides were converted to 4,5-trans-oxazolines using an
(DIETHYLAMINO)SULFUR TRIFLUORIDE (DAST) AS A USEFUL REAGENT FOR THE PREPARATION OF 2-OXAZOLINES FROM 1,2-AMIDO ALCOHOLS
Lafargue, Pierre,Guenot, Pierre,Lellouche, Jean-Paul
, p. 947 - 958 (2007/10/02)
Acylic 1,2-amido alcohols (6) react efficiently with a slight excess of (diethylamino)sulfur trifluoride (DAST) to afford the corresponding 2-oxazolines (10) in good yields ranging between 57-95percent.Even at the low temperature of -78 deg C, a rapid ( 1 h) and stereoselective amide cyclization is observed without formation of acylaziridine by-products.The scope of this cyclization is discussed.