Details

Autor(en) / Beteiligte

• Yu, Zhang-Long
• Cheng, Yong-Feng
• Jiang, Na-Chuan
• Wang, Jian
• Fan, Li-Wen
• Yuan, Yue
• Li, Zhong-Liang
• Gu, Qiang-Shuai
• Liu, Xin-Yuan

Titel

Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination

Ist Teil von

• Chemical science (Cambridge), 2020-06, Vol.11 (23), p.5987-5993

Ort / Verlag

Cambridge: Royal Society of Chemistry

Erscheinungsjahr

2020

Link zum Volltext

Quelle

EZB Free E-Journals

Beschreibungen/Notizen

• Although great success has been achieved in catalytic asymmetric hydroamination of unactivated alkenes using transition metal catalysis and organocatalysis, the development of catalytic desymmetrising hydroamination of such alkenes remains a tough challenge in terms of attaining a high level of stereocontrol over both remote sites and reaction centers at the same time. To address this problem, here we report a highly efficient and practical desymmetrising hydroamination of unactivated alkenes catalysed by chiral Brønsted acids with both high diastereoselectivity and enantioselectivity. This method features a remarkably broad alkene scope, ranging from mono-substituted and gem -/1,2-disubstituted to the challenging tri- and tetra-substituted alkenes, to provide access to a variety of diversely functionalized chiral pyrrolidines bearing two congested tertiary or quaternary stereocenters with excellent efficiency under mild and user-friendly synthetic conditions. The key to success is indirect activation of unactivated alkenes by chiral Brønsted acids via a concerted hydroamination mechanism.