Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters

被引:219
作者
Wang, Zhaobin [1 ]
Wong, Yuk Fai [1 ]
Sun, Jianwei [1 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
asymmetric catalysis; heterocycles; nucleophilic addition; organocatalysis; synthetic methods; CONJUGATE ADDITION; TRIARYLMETHANES; BIOSYNTHESIS; ALKYLATION; ALKALOIDS; POLYMERS; INDOLES; ACCESS;
D O I
10.1002/anie.201506701
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Described herein is a general and mild catalytic asymmetric 1,6-conjugate addition of para-quinone methides (p-QMs), a class of challenging reactions with previous limited success. Benefiting from chiral BrOnsted acid catalysis, which allows insitu formation of p-QMs, our reaction expands the scope to general p-QMs with various substitution patterns. It also enables efficient intermolecular formation of all-carbon quaternary stereocenters with high enantioselectivity.
引用
收藏
页码:13711 / 13714
页数:4
相关论文
共 69 条
[1]   SYNTHESIS OF DIHYDRO-1H-INDENES VIA A FORMAL 3+2-CYCLOADDITION OF PARA-QUINONE METHIDES AND STYRENES [J].
ANGLE, SR ;
ARNAIZ, DO .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3708-3710
[2]   FORMATION OF CARBON-CARBON BONDS VIA QUINONE METHIDE-INITIATED CYCLIZATION REACTIONS [J].
ANGLE, SR ;
ARNAIZ, DO ;
BOYCE, JP ;
FRUTOS, RP ;
LOUIE, MS ;
MATTSONARNAIZ, HL ;
RAINIER, JD ;
TURNBULL, KD ;
YANG, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6322-6337
[3]   PARA-QUINONE METHIDE INITIATED CYCLIZATION REACTIONS [J].
ANGLE, SR ;
TURNBULL, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1136-1138
[4]  
[Anonymous], 2014, ANGEW CHEM-GER EDIT
[5]  
[Anonymous], 1974, CHEM QUINONOID COMPO
[6]  
[Anonymous], 2013, Angew. Chem.
[7]  
[Anonymous], 2009, Angew. Chem
[8]  
[Anonymous], 2015, ANGEW CHEM, V127, P7814
[9]  
[Anonymous], ANGEW CHEM
[10]   NBS-promoted reactions of symmetrically hindered methylphenols via p-benzoquinone methide [J].
Baik, W ;
Lee, HJ ;
Jang, JM ;
Koo, S ;
Kim, BH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) :108-115