Journal
ORGANIC LETTERS
Volume 2, Issue 20, Pages 3165-3168Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0063611
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[GRAPHICS] Hetero Diels-Alder (HDA) cycloaddition of chiral 1-p-tolylsulfinyl-1,3-pentadiene with benzyl nitrosoformate, under mild conditions, yields 2H-1,2-oxazine 3 with complete regioselectivity and pi-facial diastereoselectivity. Sequential osmylation and protection of the resulting glycol gives the oxazine 5 which is directly transformed into enantiomerically pure 1,4,5 trideoxy-1,4-imino L-ribitol 8 by reduction under Pd/C.
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