期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 33, 页码 11483-11490出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201905475
关键词
enantioselectivity; homoenolates; N-heterocyclic carbenes; organocatalysis; synthons
资金
- Australian Research Council [DP170103567] Funding Source: Medline
Direct polarity inversion of conjugate acceptors provides a valuable entry to homoenolates. N-heterocyclic carbene (NHC) catalyzed reactions, in which beta-unsubstituted conjugate acceptors undergo homoenolate formation and C-C bond formation twice, have been developed. Specifically, the all-carbon (5+1) annulations give a range of mono- and bicyclic cyclohexanones (31 examples). In the first family of annulations, beta-unsubstituted acrylates tethered to a divinyl ketone undergo cycloisomerization, providing hexahydroindenes and tetralins. In the second, partially untethered substrates undergo an intermolecular (5+1) annulation involving dimerization followed by cycloisomerization. While enantioselectivity was not possible with the former, the latter proved viable, allowing cyclohexanones to be produced with high levels of enantiopurity (most >95:5 e.r.) and exclusive diastereoselectivity (>20:1 d.r.). Derivatizations and mechanistic studies are also reported.
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