Chemistry and Chemical Bioengineering Unit (Kyoto Lab), Okinawa Institute of Science and Technology Graduate University, Mikuruma, 448-5 Kajii, Kamigyo, Kyoto 602-0841, Japan.
Chemistry. 2013 May 10;19(20):6213-6. doi: 10.1002/chem.201300595. Epub 2013 Apr 4.
Organocatalytic formal hetero-Diels-Alder reactions of enones with isatins, which gave highly enantiomerically enriched functionalized spirooxindole tetrahydropyranones via an enamine-based mechanism, were developed. The catalyst systems were identified by a screen of combinations of amines, acids, and additives. With the identified catalyst systems, various spirooxindole tetrahydropyranones were synthesized in high yields with high diastereo- and enantioselectivities (see scheme).
发展了一种通过烯胺机理实现的高对映选择性官能化螺[氧化吲哚]-四氢吡喃酮的有机催化形式杂[4+2]环加成反应，其中包括烯酮与色满酮的反应。通过对胺、酸和添加剂的组合进行筛选，确定了催化剂体系。在确定的催化剂体系中，各种螺[氧化吲哚]-四氢吡喃酮以高产率和高非对映选择性和对映选择性合成（见方案）。
