Asymmetric synthesis of spiro-3,4-dihydropyrans via a domino organocatalytic sequence.
A cinchona alkaloid-catalyzed domino Michael/hemiacetalization reaction of cyclic beta-oxo aldehydes and aromatic beta,gamma-unsaturated alpha-keto esters, resulting in the formation of spiro-dihydropyran architectures in good yield with high stereoselectivity (up to 97% ee), is presented.
Yao
Weijun
W
Department of Chemistry, Zhejiang University, 20 Yugu Road, Hangzhou 310027, People's Republic of China.
Pan
Lianjie
L
Wu
Yihua
Y
Ma
Cheng
C
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D011714:Pyrans; D013141:Spiro Compounds; C073813:3,4-dihydropyran