Institute of Chemical Biology, Henan University, Kaifeng, Henan, People's Republic of China 475004.
Org Lett. 2012 Sep 7;14(17):4670-3. doi: 10.1021/ol3021176. Epub 2012 Aug 24.
An organocatalytic asymmetric sulfenylation of 3-aryloxindoles with N-(sulfanyl)succinimides has been developed by using commercially available (DHQD)(2)PHAL as catalyst. Various chiral 3-benzylthio-, alkylthio-, and arylthio-substituted oxindoles, containing 3,3-disubstituted quarternary carbon stereocenters, could be obtained in high enantioselectivities (85-97% ee). Furthermore, the opposite enantiomers of the sulfenylated products were readily accessible with equal excellent enantioselectivities (86-95% ee) by replacing the catalyst with (DHQ)(2)PHAL.
一种使用商业可得的(DHQD)(2)PHAL 作为催化剂的 3-芳基氧化吲哚与 N-(硫基)琥珀酰亚胺的不对称有机催化硫代反应已经被开发出来。各种手性 3-苄基硫代、烷基硫代和芳基硫代取代的氧化吲哚,含有 3,3-二取代的季碳立体中心,可以以高对映选择性(85-97%ee)获得。此外,通过用(DHQ)(2)PHAL 替换催化剂,很容易获得硫代产物的对映异构体,对映选择性相同(86-95%ee)。