173065-24-2Relevant articles and documents
Stereoselective synthesis of (R)-(-)-2,2-dimethyl-3-t-butoxycarbonyl-4-ethynyloxazolidine: A chiral building block for the synthesis of a new class of substituted alkynes
Reginato, Gianna,Mordini, Alessandro,Degl'Innocenti, Alessandro,Caracciolo, Massimo
, p. 8275 - 8278 (1995)
(R)-(-)-2,2-Dimethyl-3-t-butoxycarbonyl-4-ethynyl-oxazolidine (3a) has been prepared in good yield from chiral aminoaldehyde (4) through a two step procedure. Metalation of compound (3a) and subsequent reaction with electrophiles has been investigated lea
Synthetic Elaboration of the Side Chain of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: A New Regio- And Stereoselective Strategy to δ-Functionalized β-Amino Alcohols
Reginato, Gianna,Mordini, Alessandro,Caracciolo, Massimo
, p. 6187 - 6192 (2007/10/03)
An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.