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- Title
Organocatalytic Enantioselective Synthesis of 1,3‐Oxazinanes and Hexahydropyrimidines via [4+2]‐Annulation of Cyclic N‐Sulfimines.
- Authors
Yeon Kim, Seung; Kim, Yoseop; Kim, Sung‐Gon
- Abstract
The first asymmetric synthetic method for enantioenriched 1,3‐oxazinane and hexahydropyrimidine derivatives via the asymmetric [4+2]‐annulation of cyclic N‐sulfimines has been established. The reaction of cyclic N‐sulfimines with δ‐hydroxy‐α,β‐unsaturated ketones afforded a wide range of enantioenriched polyheterotricyclic 1,3‐oxazinane derivatives in high yields with good to excellent enantioselectivities in the presence of a cinchonidine‐derived squaramide catalyst. This approach has been extended to the asymmetric organocatalytic [4+2]‐annulation of cyclic N‐sulfimines with δ‐NHTs‐α,β‐unsaturated ketones providing enantioenriched hexahydropyrimidines. In addition, the asymmetric [4+2]‐annulation of δ‐hydroxy‐ and δ‐NHTs‐α,β‐unsaturated ketones gave their corresponding enantioenriched 1,3‐oxazinane and hexahydropyrimidine derivatives with different absolute configurations.
- Subjects
KETONES; CATALYSTS; ANNULATION
- Publication
Asian Journal of Organic Chemistry, 2023, Vol 12, Issue 5, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202300022