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Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides
| Content Provider | Semantic Scholar |
|---|---|
| Author | Mcmillen, D. W. Varga, Norbert Reed, Beth Ann King, Claudia |
| Copyright Year | 2000 |
| Abstract | The asymmetric copper-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl sulfides (2a−i) were reacted with ethyl diazoacetate in the presence of copper triflate (CuOTf) and a C2-symmetric bis-oxazoline ligand (5a−c). The degree of asymmetric induction ranged from 2.8% for allyl methyl sulfide (2a) to 60% for (1S,2S,5R)-(+)-allyl menthyl sulfide (2d). The enantioselectivity of the reactions was also dependent on the electronic nature of the sulfide; allyl phenyl sulfide (2e) gave a 14% ee, whereas allyl p-methoxyphenyl sulfide (2i) produced only an 8% ee. The stereochemistry of 2d and (1R,2S,5R)-(+)-allyl menthyl sulfide (7) was assigned on the basis of NMR spectroscopic experiments. |
| Starting Page | 2532 |
| Ending Page | 2536 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/jo991842n |
| Volume Number | 65 |
| Alternate Webpage(s) | http://polymer.chem.cmu.edu/~kmatweb/2000/April_00/JOC/JOC3.pdf |
| Alternate Webpage(s) | https://doi.org/10.1021/jo991842n |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
