Journal
SYNLETT
Volume 27, Issue 7, Pages 1068-1072Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1561843
Keywords
N-heterocyclic carbenes; noncovalent catalysis; sulfa-Michael; organocatalysis; asymmetric synthesis
Categories
Funding
- National Natural Science Foundation of China [21372013, 21572004]
- Shenzhen Peacock Program [KQTD201103]
- Disciplinary Development Program for Chemical Biology by the Shenzhen Municipal Development and Reform Commission
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We report an asymmetric sulfa-Michael reaction of ,-unsaturated amides and esters using a chiral N-heterocyclic carbene as the HOMO-raising organocatalyst. We discovered an interesting correlation between C-13 NMR shifts of substrates and ee of their products. More electron-deficient Michael acceptors afforded higher enantioselectivity.
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