Diastereoselective synthesis of 1,3-disubstituted isoindolines and sultams via bronsted acid catalysis

• Published in: Chemical communications (Cambridge, England) Vol. 54; no. 80; pp. 11292 - 11295
• Main Authors: Tao, Ye, Gilbertson, Scott R.
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 04.10.2018; Royal Society of Chemistry
• Subjects: Alkynes; Catalysis; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; Stereoselectivity; Trifluoromethane; BRONSTED ACID; CHIRAL HOMOPROPARGYL SULFONAMIDES; ENANTIOSELECTIVE SYNTHESIS; NITROGEN-HETEROCYCLES; A-C; HYDROAMINATION; ALKYNES; EFFICIENT; CYCLIZATION

The bis(trifluoromethane)sulfonimide (Tf2NH) catalyzed intramolecular hydroamidation of terminal alkynes is reported. The combination of Et3SiH and Tf2NH provides cis-1,3-disubstituted isoindolines and sultams in high yield (up to 98%) and high diastereoselectivity (up to 99:1 d.r.).