83092-37-9Relevant articles and documents
Binolam-AlCl: A two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates
Baeza, Alcjandro,Najera, Carmen,Sansano, Jose M.,Saa, Jose M.
, p. 3849 - 3862 (2005)
The enantioselective synthesis of cyanohydrin O-phosphates by using in situ generated bifunctional catalysts (R)- or (S)-3,3′-bis(diethylaminomethyl) -1, 1′-binaphthol-aluminium chloride (binolam-AlCl) is reported. The reaction, which can be described as an overall cyano-O-phosphorylation of aldehydes, has a wide scope and applicability. Evidence is also provided, including ab initio and DFT calculations, in support of supported by the Lewis acid/Bronsted base (LABB) dual role of the catalyst in inducing first the key enantioselective hydrocyanation, which is then followed by O-phosphorylation. A brief screening of the synthetic usefulness of the resulting cyanohydrin O-phosphates unveiles some interesting applications. Among them, chemoselective hydrolysis, reduction and palladium-catalysed nucleophilic allyl substitution, thereby leading to enantiomerically enriched α-O-phosphorylated α-hydroxy esters, β-amino alcohols and γ-cyanoallyl alcohols, respectively. Naturally occurring (-)-tembamide and (-)-aegeline are synthesised accordingly.
