Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 7, Issue 21, Pages 4539-4546Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b910835a
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Funding
- National Natural Science Foundation of China [NSFC 20772110]
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The asymmetric tandem oxa-Michael-aldol reaction of salicylic aldehyde derivatives with alpha,beta-unsaturated aldehydes catalyzed by a chiral amine/chiral acid organocatalytic system was investigated. The organocatalytic system of (S)-diphenylpyrrolinol trimethylsilyl ether with chiral shift reagent (S)-Mosher acid presented a synergistic effect in the improvement of reaction performance and offered an efficient steric effect in the transformation. The tandem oxa-Michael-aldol reaction proceeded with high yields (up to 90%) and with excellent ee values (up to 99%) to give the corresponding chromene derivatives. The structure of the chiral ammonium salt formed in situ and the corresponding mechanism were also studied by H-1 NMR.
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