Journal
CHEMICAL RECORD
Volume 22, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.202100161
Keywords
Intramolecular aza-Michael reaction; asymmetric synthesis; nitrogen heterocycles; organocatalysis; sulfinyl amines
Categories
Funding
- Spanish Ministerio de Economia y Competitividad [PID2020-115294GB-I00]
- Spanish Ministerio de Educacion, Cultura y Deporte [FPU16/04533, FPU18/02750]
Ask authors/readers for more resources
The asymmetric intramolecular aza-Michael reaction (IMAMR) is a convenient strategy for generating heterocycles with nitrogen-substituted stereocenters, finding widespread applications in the total synthesis of alkaloids and biologically relevant compounds. Recent developments in asymmetric versions of IMAMR mainly involve the use of organocatalysts, such as chiral imidazolidinones and diaryl prolinol derivatives. The use of N-sulfinyl imines with dual roles has also emerged as a versatile mode for performing the asymmetric IMAMR.
The asymmetric intramolecular aza-Michael reaction (IMAMR) is a very convenient strategy for the generation of heterocycles bearing nitrogen-substituted stereocenters. Due to the ubiquitous presence of these skeletons in natural products, the IMAMR has found widespread applications in the total synthesis of alkaloids and biologically relevant compounds. The development of asymmetric versions of the IMAMR are quite recent, most of them reported in this century. The fundamental advances in this field involve the use of organocatalysts. Chiral imidazolidinones, diaryl prolinol derivatives, Cinchone-derived primary amines and quaternary ammonium salts, and BINOL-derived phosphoric acids account for the success of those methodologies. Moreover, the use of N-sulfinyl imines with a dual role, as nitrogen nucleophiles and as chiral auxiliaries, appeared as a versatile mode of performing the asymmetric IMAMR.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available