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Stereoselective heterocycle synthesis through a reversible allylic alcohol transposition and nucleophilic addition sequence
| Content Provider | Semantic Scholar |
|---|---|
| Author | Xie, Youwei Floreancig, Paul E. |
| Copyright Year | 2011 |
| Abstract | The abilities of Re2O7 to promote non-stereoselective allylic alcohol transposition reactions and acetal ionization or enone activation have been coupled for a heterocycle synthesis in which thermodynamics dictate stereochemical outcomes. The stabilities of intermediate allylic cation and oxocarbenium ion intermediates dictate the efficiency of product equilibration. Long range stereoinduction can be observed in the synthesis of spiroketals and spirotricycles through this protocol. |
| Starting Page | 2423 |
| Ending Page | 2427 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/C1SC00570G |
| Volume Number | 2 |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/sc/c1/c1sc00570g/c1sc00570g.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/C1SC00570G |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |