Highly Regio‐ and Enantioselective Nitroso Diels−Alder Reaction of 1,3‐Diene‐1‐carbamates Catalyzed by Chiral  N,N′ ‐Dioxide/Copper(II) Complex | Zendy

Lu Yan | Zendy; Zhou Yuhang | Zendy; Zhang Jingchuan | Zendy; Lin Lili | Zendy; Liu Xiaohua | Zendy; Feng Xiaoming | Zendy

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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.

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