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cis-Enals in N-heterocyclic carbene-catalyzed reactions : distinct stereoselectivity and reactivity †
| Content Provider | Semantic Scholar |
|---|---|
| Author | Chen, Xingkuan Fang, Xinqiang Chi, Yonggui Robin |
| Copyright Year | 2013 |
| Abstract | Homoenolate has been an important intermediate in both mechanistic and synthetic studies since its rst report in 1962. Recently with N-heterocyclic carbene (NHC) catalysis, the generation of homoenolate equivalents from trans-enals has been proven to be a powerful approach in synthetic transformations. In principle, the formation of cis-homoenolate equivalents from the reaction of cis-enals with NHC catalysts is possible (eqn (1)). Thus, the use of cis-enals may allow the efficient access to diastereomers of reaction products that are otherwise challenging to obtain.However, in addition to their problematic synthesis, the facile isomerization of cis-enals or their intermediates to the trans isomers under catalytic conditions oen precludes their use. Nevertheless, their potential utility in providing alternative stereochemical outcomes makes them attractive starting materials for the development of new catalytic reactions. In the attempted reactions using cis-enal substrates under NHC catalysis for homoenolate generation, only products identical to those derived from the corresponding trans-enals were obtained. Here we report the rst successful employment of cis-enals in NHC-mediated cis-homoenolate generation. We have shown that |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://www3.ntu.edu.sg/home/robinchi/publication%20lists/34%20pdf.pdf |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | Attempt Bridged Bicyclo Compounds, Heterocyclic Carcinoma in Situ Catalysis Cisplatin Equivalent Weight Isomerism Source-to-source compiler Synthetic intelligence carbene cell transformation |
| Content Type | Text |
| Resource Type | Article |
