Catalytic Asymmetric [4+1] Cyclization of ortho-Quinone Methides with 3-Chlorooxindoles

被引:109
作者
Jiang, Xiao-Li [1 ]
Liu, Si-Jia [1 ]
Gu, Yu-Qi [1 ]
Mei, Guang-Jian [1 ]
Shi, Feng [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Peoples R China
基金
中国国家自然科学基金;
关键词
ortho-quinone methides; cyclization; organocatalysis; asymmetric catalysis; spirooxindole; FRIEDEL-CRAFTS REACTION; IN-SITU; ENANTIOSELECTIVE SYNTHESIS; ACTIVATION STRATEGY; ACID CATALYSIS; CYCLOADDITION; CONSTRUCTION; OXINDOLES; ANNULATION; ADDITIONS;
D O I
10.1002/adsc.201700487
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this work, we established catalytic asymmetric [4+1] cyclization of ortho-quinone methides (o-QMs) with 3-chlorooxindoles and a catalytic asymmetric domino oxidation/[4+1] cyclization reaction of 2-alkylphenols with 3-chlorooxindoles, which constructed a spirooxindole-based 2,3-dihydrobenzofuran scaffold in good yield (up to 97%), with excellent diastereoselectivity (up to > 95: 5 dr) and high enantioselectivity (up to 99% ee). This work is not only the first highly enantioselective [4+1] cyclization of o-QMs but has also realized the first catalytic asymmetric domino [4+1] cyclization of o-QMs. In addition, both of the reactions provide efficient stereoselective methods for constructing spirooxindole-based 2,3-dihydrobenzofuran scaffolds with optical purity.
引用
收藏
页码:3341 / 3346
页数:6
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