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Organocatalytic asymmetric double Michael reaction of Nazarov reagents with alkylidene azlactones for the construction of spiro-fused cyclohexanone/5-oxazolone system.
- Source :
-
Tetrahedron . Sep2014, Vol. 70 Issue 35, p5787-5793. 7p. - Publication Year :
- 2014
-
Abstract
- A bifunctional thiourea-tertiary amine-catalyzed enantioselective double Michael reaction of Nazarov reagents and alkylidene azlactones was realized. Using this protocol, a series of optically active spiro-fused cyclohexanone/5-oxazolone derivatives, bearing three consecutive chiral centers including one spiro quaternary chiral center, were obtained in good yields with good stereoselectivities (up to 93% yield, 99:1 dr, and 91% ee). The synthetic utility of the products for the formation of chiral cyclic quaternary amino-acid derivatives was also demonstrated. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 70
- Issue :
- 35
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 97186446
- Full Text :
- https://doi.org/10.1016/j.tet.2014.06.042