Alkyl, Alkenyl, and Alkynyl Group Additions

Since organoaluminums are highly oxophilic, the reaction of organoaluminum compounds and various carbonyl compounds gives 1 1 Lewis acid-base complexes. In the cases of alkylaluminums and electrophilic carbonyl compounds, alkyl transfer reactions to carbonyl carbon proceed via Lewis acid-base complexes at high temperature [37, 38]. 

1 equivalent of MAD, the similar reduction gave selectively tert-butylphenylcarbinol from more hindered tert-butylphenylketone [47]. 

Cyanohydrins and their silylated analogs are one of the most useful synthetic building blocks. To obtain cyanohydrin with high optical purity, various chiral 

Recently, hydrocyanation and cyanosilylation reactions with other type of chiral aluminum complexes were reported. In 1999, Shibasaki and Kanai reported enantioselective cyanosilylation of aldehydes catalyzed by Lewis acid-Lewis base bifunctional catalyst (64a) [56, 57]. In this catalyst, aluminum center works as a Lewis acid to activate the carbonyl group, and the oxygen atom of the phosphine oxide works as a Lewis base to activate TMSCN. Asymmetric induction was explained by the proposed transition state model having the external phosphine oxide coordination to aluminum center, thus giving rise to pentavalent aluminum 

Aluminum Lewis acids can promote cyanide additions to N-acyl quinolinium and isoquinolinium, which is known as the Reissert reaction. In aprotic media, a combination of AICI3 and TMSCN was widely used [64]. In the presence of catalytic amount of AICI3, diaster eoselective Reissert reactions of isoquinolines with 

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