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Allylic alcohols: Valuable synthetic equivalents of non-activated alkenes in gold-catalyzed enantioselective alkylation of indoles
- Source :
- Journal of Organometallic Chemistry. 696:338-347
- Publication Year :
- 2011
- Publisher :
- Elsevier BV, 2011.
-
Abstract
- The recent booming of gold catalysis has demonstrated that unprecedented transformations can be realized in a highly selective manner. Moreover, due to the growing availability of chiral organic ligands, gold-catalysis can be considered as one of most dynamic hot spots in asymmetric synthesis. However, in this context, the use of non-activated olefinic C–C double bonds is still largely unexplored due to the intrinsic inertness of C C (respect to allenes and alkynes) in taking part in nucleophilic additions assisted by π-electrophilic activations. Allylic alcohols have been demonstrated to be feasible “surrogates” of non-activated alkenes for the enantioselective allylic alkylation of indoles catalyzed by chiral gold(I) complexes. In this investigation, a full account addressing efficiency and substrate scope of such a process is presented.
- Subjects :
- Allylic rearrangement
Chemistry
INDOLE
Organic Chemistry
Enantioselective synthesis
FRIEDELECRAFTS REACTION
Context (language use)
Alkylation
Biochemistry
GOLD-CATALYSIS
Catalysis
Inorganic Chemistry
Tsuji–Trost reaction
Nucleophile
Materials Chemistry
ALLYLIC ALCOHOLS
Organic chemistry
Physical and Theoretical Chemistry
Friedel–Crafts reaction
Subjects
Details
- ISSN :
- 0022328X
- Volume :
- 696
- Database :
- OpenAIRE
- Journal :
- Journal of Organometallic Chemistry
- Accession number :
- edsair.doi.dedup.....7656c3879d7de130de3439e62c5be2cd