Premium
Highly Regio‐ and Enantioselective Nitroso Diels−Alder Reaction of 1,3‐Diene‐1‐carbamates Catalyzed by Chiral N,N′ ‐Dioxide/Copper(II) Complex
Author(s) -
Lu Yan,
Zhou Yuhang,
Zhang Jingchuan,
Lin Lili,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2018
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.201701155
Subject(s) - chemistry , enantioselective synthesis , nitroso , diene , catalysis , copper , diels–alder reaction , organic chemistry , medicinal chemistry , natural rubber
A chiral N,N′ ‐dioxide/Copper(II) complex‐catalyzed highly regio‐ and enantioselective nitroso Diels−Alder (NDA) reaction of 2‐nitrosopyridines with 1,3‐diene‐1‐carbamates was described. A series of 3,6‐dihydro‐1,2‐oxazines were obtained in good to excellent yields and ee values. On the basis of the control experiments, ESI‐MS analysis and the absolute configuration of the product, a possible transition state model was proposed to explain the stereocontrol.