Organocatalytic enantioselective cascade Michael-Michael-Wittig reactions of phosphorus ylides: one-pot synthesis of the all-cis trisubstituted cyclohexenecarboxylates via the [1 + 2 + 3] annulation.
The stereoselective synthesis of all-cis 5-nitro-4,6-diphenylcyclohex-1-enecarboxylic ester has been achieved by an organocatalytic asymmetric Michael-Michael-Wittig cascade reaction of phosphorus ylides, nitroolefins, and alpha,beta-unsaturated aldehydes with excellent enantioselectivities (up to >99% ee).
Hong
Bor-Cherng
BC
Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, ROC. chebch@ccu.edu.tw
Jan
Rei-Hau
RH
Tsai
Chih-Wei
CW
Nimje
Roshan Y
RY
Liao
Ju-Hsiou
JH
Lee
Gene-Hsiang
GH
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
C546295:5-nitro-4,6-diphenylcyclohex-1-enecarboxylic ester; D000447:Aldehydes; D000475:Alkenes; D053138:Cyclohexenes; D009574:Nitro Compounds; D009943:Organophosphorus Compounds