Back to Search
Start Over
Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine.
- Source :
-
Organic letters [Org Lett] 2007 Oct 25; Vol. 9 (22), pp. 4559-62. Date of Electronic Publication: 2007 Sep 26. - Publication Year :
- 2007
-
Abstract
- Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or alpha,beta-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenylsulfonyl)-alpha-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (-)-metazocine.
Details
- Language :
- English
- ISSN :
- 1523-7060
- Volume :
- 9
- Issue :
- 22
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 17894504
- Full Text :
- https://doi.org/10.1021/ol702019b