Alanal, reaction with sodium cyanide

CHLOROACETONITRILE or o-CHLOROACETONITRILE or 2-CHLOROACETONITRILE (107-14-2) ClCHjCN Forms explosive mixture with air (flash point 133°F/56°C Fire Rating 2). Contact with water, steam, or strong acid, or acid fumes produce toxic hydrogen cyanide gas. Violent reaction with strong oxidizers. Incompatible with sodium nitrate, lithium alanate. Thermal decomposition releases toxic hydrogen cyanide and hydrogen chloride gas. On small fires, use dry... 

CHLOROACETONITRILE (107-14-2) Forms explosive mixture with air (flash point 133°F/56°C). Contact with steam or acids produces hydrogen cyanide gas. Violent reaction with strong oxidizers. Incompatible with sodium nitrate, lithium alanate. 

In the synthesis of (—)-lupinine (926) by Santos et al., (lR,2S,5R)-8-phenyhnenthol was used as the chiral auxiliary in controlling the stereochemical outcome of the reaction of the piperidine-containing carbamate 1042 with the 2-silyloxyfuran 1043 (Scheme 130). With trimethylsilyl triflate as Lewis acid catalyst and butyhnethylimidazolinium tetrafluorobo-rate as additive, an 80% yield was obtained as a 9.7 1 mixture in favor of threo-product (—)-1044. After hydrogenation of the double bond, treatment of the intermediate (—)-1045 with sodium methoxide effected rearrangement to the (R,R)-(- -)-l-hydroxyquinolizidin-4-one (- -)-1046 in 93% overall yield. Mitsunobu inversion of the alcohol to the (lS)-epimer (—)-1047 followed by alane reduction of the lactam afforded the quinolizi-din-l-ol (—)-1048. A second inversion at C-1 with cyanide produced the... 

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