-The regio-and enantioselective hetero Diels-Alder reaction of a nitroso compound with a cyclic dienol, cyclohexa-1,3-dienylmethanol, has been realized utilizing stoichiometric amount of tartaric acid ester as a chiral auxiliary to afford the corresponding dihydro-1,2-oxazine with complete regioselectivity and high enantioselectivity of up to 92% ee.A catalytic version of the asymmetric hetero Diels-Alder reaction of nitroso compounds with the dienol was also achieved to afford the corresponding optically active cycloadducts with up to 83% ee. The addition of MS 4A was crucial to realize reproducible high enantioselectivity.

Oxazine derivatives R 0595Asymmetric Hetero Diels-Alder Reaction of Nitroso Compounds Utilizing Tartaric Acid Ester as a Chiral Auxiliary. -Hetero Diels-Alder reaction of cyclic dienol (IV) with nitrosoarenes utilizing tartrate as chiral auxiliary affords dihydro--1,2-oxazines with complete regioselectivity and high enantioselectivity. -(SAKAI, H.; DING, X.; YOSHIDA, T.; FUJINAMI, S.; UKAJI*, Y.; INOMATA, K.; Heterocycles 76 (2008) 2, 1285-1300; Div. Mater. Sci., Grad. Sch. Nat. Sci. Technol., Kanazawa Univ., Kanazawa 920, Japan; Eng.) -D. Singer 18-161