Asymmetric cyclopropanations and cycloadditions of dioxocarbenes
Muller, P; Allenbach, YF; Chappellet, S; Ghanem, A
| HERO ID | 4936014 |
|---|---|
| In Press | No |
| Year | 2006 |
| Title | Asymmetric cyclopropanations and cycloadditions of dioxocarbenes |
| Authors | Muller, P; Allenbach, YF; Chappellet, S; Ghanem, A |
| Journal | Synthesis |
| Issue | 10 |
| Page Numbers | 1689-1696 |
| Abstract | Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been developed. The structure of the [Rh-2{(S)-nttl}4] catalyst was optimized to produce up to 98% ee in olefin cyclopropanations with dimethyl malonate or Meldrum's acid. Highly selective Rh(II)-catalyzed olefin cyclopropanations could be observed upon replacement of methyl diazoacetoacetate by methyl (silyloxyvinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazopyruvate to polar olefins have been realized with Ru(II)-pybox catalysts. |
| Doi | 10.1055/s-2006-926452 |
| Wosid | WOS:000237721200018 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-33744462643&doi=10.1055%2fs-2006-926452&partnerID=40&md5=4f58fee0530bbc2d6c7414436fa3c3b8 |
| Is Public | Yes |
| Language Text | English |
| Keyword | carbenoids; catalysis; diazo decomposition; phenyl-iodonium ylides; rhodium |