Asymmetric Hetero Diels-Alder Reaction of Nitroso Compounds Utilizing Tartaric Acid Ester as a Chiral Auxiliary
作者:Katsuhiko Inomata、Hiroki Sakai、Xia Ding、Tetsusuke Yoshida、Shuhei Fujinami、Yutaka Ukaji
DOI:10.3987/com-08-s(n)94
日期:——
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
利用化学计量的酒石酸酯作为手性助剂,实现了亚硝基化合物与环状二烯醇环己醇-1,3-二烯基甲醇的区域和对映选择性杂狄尔斯-阿尔德反应,得到相应的二氢-1,2 -恶嗪具有完全的区域选择性和高达 92% ee 的高对映选择性。还实现了亚硝基化合物与二烯醇的不对称杂 Diels-Alder 反应的催化形式,以提供高达 83% ee 的相应光学活性环加合物。添加 MS 4A 对于实现可重现的高对映选择性至关重要。