Amino alcohols Cyanotrimethylsilane

Amino alcohols Cyanotrimethylsilane, 87 Lithium aluminum hydride-Sodium... 

Cleavage of oxetanes.2 In the presence of Znl2, oxetanes are opened by cyanotrimethylsilane regioselectively to y-hydroxy isocyanides, which undergo acid-catalyzed hydrolysis to y-amino alcohols. 

The ambident nature of cyanotrimethylsilane can lead to the formation of nitriles or isocyanides, depending on the nature of the catalyst. For example, cyanotrimethylsilane reactions with epoxides and oxetanes catalyzed by soft Lewis acids give rise to 2-(trimethylsiloxy) isocyanides arising by attack on the more substituted carbon (eqs 15 and 16).Milder reaction conditions and better yields of isocyanides can be realized when the reaction of cyanotrimethylsilane with oxiranes is carried out in the presence of Pd(CN)2, SnCL, or MesGa (eq 17). Isocyanides are useful precursors for the synthesis of /3-amino alcohols and oxazolines. 

Other methods to form carboxylic acids Cyanotrimethylsilane, 87 a-Substituted carboxylic acids (see also Amino acids, Halo carbonyl compounds, Hydroxy acids) Camphor-10-sulfonic acid, 62 Chiral compounds Alcohols... 

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