1104587-88-3Relevant academic research and scientific papers
Asymmetric hetero diels-alder reaction of nitroso compounds utilizing tartaric acid ester as a chiral auxiliary
Sakai, Hiroki,Ding, Xia,Yoshida, Tetsusuke,Fujinami, Shuhei,Ukaji, Yutaka,Inomata, Katsuhiko
experimental part, p. 1285 - 1300 (2009/06/28)
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.
