Journal
ORGANIC LETTERS
Volume 23, Issue 7, Pages 2790-2796Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00709
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Funding
- National Natural Science Foundation of China [21901072, 21772038]
- Shanghai Sailing Program [18YF1405600]
- Research Center of Analysis and Test of East China University of Science and Technology
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An iridium-catalyzed trifluoroacetic acid-promoted asymmetric cascade allylation/Pictet-Spengler cyclization reaction of azomethine ylides with aromatic allylic alcohols is reported, providing a facile and scalable method for the construction of 1,3,4-trisubstituted tetrahydroisoquinolines containing two stereogenic centers in good yields with generally excellent diastereo- and enantioselectivities. Additionally, a series of aromatic heterocyclefused piperidines were also obtained with excellent enantiocontrol by this methodology.
An iridium-catalyzed trifluoroacetic acid-promoted asymmetric cascade allylation/Pictet-Spengler cyclization reaction of azomethine ylides with aromatic allylic alcohols is reported. This protocol provides a facile and scalable method for the construction of 1,3,4-trisubstituted tetrahydroisoquinolines containing two stereogenic centers in good yields (up to 96%) with generally excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). Furthermore, a series of aromatic heterocyclefused piperidines were also obtained with excellent enantiocontrol by this methodology.
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