Stereoselective synthesis of 2,5-disubstituted pyrrolidines via gold-catalysed anti-Markovnikov hydroamination-initiated tandem reactions

• Published in: Chemical communications (Cambridge, England) Vol. 55; no. 67; pp. 9923 - 9926
• Main Authors: Tan, Tong-De, Chen, Yang-Bo, Yang, Ming-Yang, Wang, Jia-Le, Su, Hao-Ze, Hong, Feng-Lin, Zhou, Jin-Mei, Ye, Long-Wu
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 15.08.2019; Royal Society of Chemistry
• Subjects: Allyl compounds; allylation; Cascade chemical reactions; catalytic activity; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Crystallography; diastereoselectivity; enantioselectivity; Gold; Physical Sciences; pyrrolidines; Science & Technology; stereoselective synthesis; Stereoselectivity; Sulfonamides; FUNCTIONALIZATION; INTERMOLECULAR REACTION; CHIRAL HOMOPROPARGYL SULFONAMIDES; EFFICIENT SYNTHESIS; CASCADE SYNTHESIS; TERMINAL ALKYNES; RAPID ACCESS; CYCLOISOMERIZATION; OXIDATIVE CYCLIZATION; HIGHLY EFFICIENT

A series of gold-catalysed intramolecular anti-Markovnikov hydroamination-initiated azidation, allylation and heteroarylation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 2,5-disubstituted pyrrolidines are obtained in moderate to excellent yields with e...