| Autor: |
Cong H; Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States., Fu GC |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of the American Chemical Society [J Am Chem Soc] 2014 Mar 12; Vol. 136 (10), pp. 3788-91. Date of Electronic Publication: 2014 Feb 27. |
| DOI: |
10.1021/ja500706v |
| Abstrakt: |
As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if β-migratory insertion proceeds faster than direct cross-coupling, an additional carbon-carbon bond and stereocenter can be formed. With the aid of a nickel/diamine catalyst (both components are commercially available), we have established the viability of this approach for the catalytic asymmetric synthesis of 2,3-dihydrobenzofurans and indanes. Furthermore, we have applied this new method to the construction of the dihydrobenzofuran core of fasiglifam, as well as to a cross-coupling with a racemic alkyl electrophile; in the latter process, the chiral catalyst controls two stereocenters, one that is newly generated in a β-migratory insertion and one that begins as a mixture of enantiomers. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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