First Asymmetric Hetero Diels−Alder Reaction of 1-Sulfinyl Dienes with Nitroso Derivatives. A New Entry to the Synthesis of Optically Pure 1,4-Imino-l-ribitol Derivatives
- 15 September 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (20), 3165-3168
- https://doi.org/10.1021/ol0063611
Abstract
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 π-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.Keywords
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