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An environmentally benign synthesis of cis-2,6-disubstituted tetrahydropyrans via indium-mediated tandem allylation/Prins cyclization reaction.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Pham, Minh Allatabakhsh, Amir Minehan, Thomas G. |
| Copyright Year | 2008 |
| Abstract | In the presence of indium metal, 3-iodo-2-[(trimethylsilyl)methyl]propene (1) reacts with sequentially added aldehydes to provide cis-2,6-disubstituted tetrahydropyrans in good yields. Evidence suggests that InI, formed upon aldehyde (R1CHO) allylation in aqueous media, acts as a promoter for the silyl-Prins reaction with the second equivalent of added aldehyde (R2CHO). The preparation of cyclohexenyl-fused pyrans via this one-pot, three-component coupling process is presented, as is a short formal synthesis of (+/-)-centrolobine. |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://tminehan.com/Research/jo7016857cis.pdf |
| PubMed reference number | 18095701v1 |
| Volume Number | 73 |
| Issue Number | 2 |
| Journal | The Journal of organic chemistry |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | Acetaldehyde Aldehydes Cyclization Heterocyclic Compounds, Fused-Ring Indium Marijuana Abuse Primed In Situ Labeling Pyrans |
| Content Type | Text |
| Resource Type | Article |