We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Chiral DMAP‐N‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement.
- Authors
Xie, Ming‐Sheng; Zhang, Ye‐Fei; Shan, Meng; Wu, Xiao‐Xia; Qu, Gui‐Rong; Guo, Hai‐Ming
- Abstract
A DMAP‐N‐oxide, featuring an α‐amino acid as the chiral source, was developed, synthesized and applied in asymmetric Steglich rearrangement. A series of O‐acylated azlactones afforded C‐acylated azlactones possessing a quaternary stereocenter in high yields (up to 97 % yield) and excellent enantioselectivities (up to 97 % ee). Compared to the widespread use of pyridine nitrogen, which serves as the nucleophilic site in the asymmetric acyl transfer reaction, we discovered that chiral DMAP‐N‐oxides, in which the oxygen now acts as the nucleophilic site, are efficient acyl transfer catalysts. Our finding might open a new door for the development of chiral DMAP‐N‐oxides for asymmetric acyl transfer reactions.
- Subjects
AMINO acids; ENANTIOSELECTIVE catalysis; CHEMICAL reactions; CATALYSTS; RING formation (Chemistry)
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 9, p2865
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201812864