Journal
ORGANIC LETTERS
Volume 18, Issue 3, Pages 428-431Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03471
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Funding
- National Natural Science Foundation of China [NSFC21572272, NSFC21502232]
- Natural Science Foundation of Jiangsu Province [BK20140655]
- Foundation of State Key Laboratory of Natural Medicines [ZZJQ201306]
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A chiral thiourea catalyzed asymmetric 1,6-conjugate addition of para-quinone methides with dicyanoolefins has been developed. The reaction provided an efficient approach to the synthesis of chiral diarylmethine skeletons in good yields (up to 99% yield) with high diastereo- and enantioselectivity (>20:1 dr and up to 99.5:0.5 er), also on a gram scale. The preliminary mechanistic study showed that the remote stereocontrol was achieved through intermolecular hydrogen-bond interaction between the chiral thiourea catalyst and the para-quinone methides directly for the first time.
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