Asymmetric Hetero Diels-Alder Reaction of Nitroso Compounds Utilizing Tartaric Acid Ester as a Chiral Auxiliary

Abstract

The regio- and enantioselective hetero Diels-Alder reaction of a nitroso compound with a cyclic dienol, cyclohexa-l,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.