Premium
Umpolung of Hemiaminals: Titanocene‐Catalyzed Dehydroxylative Radical Coupling Reactions with Activated Alkenes
Author(s) -
Zheng Xiao,
Dai XiJie,
Yuan HongQiu,
Ye ChenXi,
Ma Jie,
Huang PeiQiang
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201210088
Subject(s) - chemistry , umpolung , cyclopentadienyl complex , radical cyclization , catalysis , medicinal chemistry , combinatorial chemistry , computer science , organic chemistry , nucleophile
Radical measures : A radical coupling reaction, which is proposed to proceed through in situ chlorination of a hydroxy group by Me 3 SiCl, is used to form quaternary carbon centers with amino groups in α position. The reaction can be scaled up and is used in an efficient six‐step total synthesis of (±)‐9,10‐diepi‐stemoamide (see scheme, Cp=cyclopentadienyl, EWG=electron‐withdrawing group).
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom