Anti-selective direct catalytic asymmetric aldol reaction of thiolactams.
An anti-selective direct catalytic asymmetric aldol reaction of thiolactam is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprised of mesitylcopper/(R,R)-Ph-BPE exhibited high catalytic performance to produce an anti-aldol product with high stereoselectivity. The highly chemoselective nature of the present catalysis allows for the use of enolizable aldehydes as aldol acceptors. The diverse transformations of the thiolactam moiety highlight the synthetic utility of the present anti-aldol protocol.
Institute of Microbial Chemistry, Tokyo, 3-14-23 Kamiosaki, Tokyo 141-0021, Japan.
Devarajulu
D
Sureshkumar
Yuji
Y
Kawato
Mitsutaka
M
Iwata
Naoya
N
Kumagai
Masakatsu
M
Shibasaki
D002384:Catalysis; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D007769:Lactams; D013438:Sulfhydryl Compounds