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Design of C3‐Alkenyl‐Substituted 2‐Indolylmethanols for Catalytic Asymmetric Interrupted Nazarov‐Type Cyclization
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-01-04 , DOI: 10.1002/adsc.201701521
Cong-Shuai Wang 1 , Jia-Le Wu 1 , Can Li 1 , Lin-Zhi Li 1 , Guang-Jian Mei 1 , Feng Shi 1
Affiliation  

The C3‐alkenyl‐substituted 2‐indolylmethanols have been designed as a new class of substrates for catalytic asymmetric interrupted Nazarov‐type cyclizations. In the presence of chiral phosphoric acid as a mild chiral Brønsted acid, the interrupted Nazarov‐type cyclization of C3‐alkenyl‐substituted 2‐indolylmethanols with nucleophiles occurred smoothly to construct cyclopenta[b]indole frameworks in generally excellent diastereo‐ and enantioselectivities (up to >95:5 dr, >99% ee).

中文翻译:

用于催化不对称中断Nazarov型环化反应的C3-链烯基取代的2-吲哚基甲醇的设计

C3-烯基取代的2-吲哚基甲醇被设计为催化不对称间断Nazarov型环化反应的新型底物。在存在手性磷酸作为温和的手性布朗斯台德酸的情况下,C3-烯基取代的2-吲哚基甲醇与亲核试剂的间断Nazarov型环化顺利发生,从而以通常优异的非对映异构和对映选择性(如上式)构建环戊[ b ]吲哚骨架到> 95:5 dr,> 99%ee)。
更新日期:2018-01-04
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