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Asymmetric cyano-ethoxycarbonylation of aldehydes catalyzed by self-assembled titanium catalyst
- Source :
-
Tetrahedron . Aug2007, Vol. 63 Issue 33, p7935-7941. 7p. - Publication Year :
- 2007
-
Abstract
- Abstract: A new self-assembled catalyst based on titanium complex has been developed for the effective enantioselective cyano-ethoxycarbonylation of aldehydes. The self-assembled catalyst was readily prepared from (R)-3,3′-bis((methyl((S)-1-phenylethyl)amino)methyl)-1,1′-binaphthyl-2,2′-diol (1h), N-((1S,2R)-2-hydroxy-1,2-diphenylethyl)acetamide (2b), and tetraisopropyl titanate (Ti(OiPr)4). A variety of aromatic aldehydes, aliphatic aldehydes, and α,β-unsaturated aldehydes were found to be suitable substrates in the presence of the self-assembled titanium catalyst (5mol% 1h, 5mol% 2b, and 5mol% Ti(OiPr)4). The desired cyanohydrin ethyl carbonates were afforded with high isolated yields (up to 95%) and moderate to good enantioselectivities (up to 92% ee) under mild conditions (at −15°C). A possible catalytic cycle based on the experimental observation was proposed. [Copyright &y& Elsevier]
- Subjects :
- *ASYMMETRIC synthesis
*CATALYSIS
*TITANIUM
*SURFACE chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 63
- Issue :
- 33
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 25618330
- Full Text :
- https://doi.org/10.1016/j.tet.2007.05.060