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Synthesis of 3‐Aryl‐1‐trifluoromethyltetrahydroisoquinolines by Brønsted Acid‐Catalyzed C( sp 3 )H Bond Functionalization
Author(s) -
Mori Keiji,
Umehara Nobuaki,
Akiyama Takahiko
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400775
Subject(s) - chemistry , surface modification , hydride , aryl , catalysis , medicinal chemistry , trifluoromethyl , brønsted–lowry acid–base theory , organic chemistry , alkyl , hydrogen
Abstract A concise route to 3‐aryl‐1‐trifluoromethyltetrahydroisoquinolines by a benzylic [1,5]‐hydride shift‐mediated CH bond functionalization was developed. The [1,5]‐hydride shift of the benzylic C( sp 3 )H bond to the trifluoromethylketimine derived from para ‐anisidine occurred smoothly to produce cis ‐1‐trifluoromethyl‐3‐aryltetrahydroisoquinolines in good to excellent chemical yields with good diastereoselectivities. In contrast, use of the NH ketimine furnished N ‐unprotected tetrahydroisoquinolines in good yields in favor of the trans ‐isomer.