Franklin A Davis, Kavirayani R Prasad, Patrick J Carroll
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122-2585, USA. fdavis@astro.ocis.temple.edu
The Journal of organic chemistry 2002 Nov 1Polyhydroxylated sulfinimines derived from protected 1,2-O-isopropyliden-L-threoses undergo the sulfinimine-mediated Strecker syntheses to give alpha-amino nitriles in good yield and de. A double stereodifferentiation effect was not observed and the diastereoselectivity is controlled by the absolute configuration of the sulfinyl group. Hydrolysis of the amino nitriles afforded the lactone rather than polyoxamic acid.
Franklin A Davis, Kavirayani R Prasad, Patrick J Carroll. Asymmetric synthesis of polyhydroxy alpha-amino acids with the sulfinimine-mediated asymmetric strecker reaction: 2-amino 2-deoxy L-xylono-1,5-lactone (polyoxamic acid lactone). The Journal of organic chemistry. 2002 Nov 1;67(22):7802-6
PMID: 12398506
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