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Synlett 1990; 1990(10): 636-637
DOI: 10.1055/s-1990-21195
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Chiral Oxazolidines as Templates for Stereoselective Synthesis of Chiral Homoallyl Amines

Ming-Jung Wu* , Lendon N. Pridgen
  • *SmithKline Beecham Pharmaceuticals, Synthetic Chemistry Department, P.O. Box 1539, King of Prussia, Pennsylvania 19406, USA
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Publication Date:
08 March 2002 (online)

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Nucleophilic allyl organocerium ("CH2=CHCH2CeCl2") adds to the inexpensive and readily available (4R)-2-aryl-4-phenyl-1,3-oxazolidines 4 in a highly stereocontrolled fashion to furnish (R,R)-homoallyl amines 5 [(R)-2-[(R)-1-aryl-3-butenylamino]-2-phenylethanols]. Homoallyl amines 5 may be oxidatively cleaved to ß-amino acids in high enantiomeric excess.