Subject hydroalumination

Hydroalumination is rather old chemistry about which many papers have been written. Readers can refer to specialized reviews on this subject [2, 170]. This chapter focuses on the recent application of hydroalumination in selective organic synthesis. 

There is a far-reaching analogy between the addition of dialkylaluminum hydrides to olefins (hydroalumination) and Brown s hydroboration reaction, and in particular the third stage of hydroboration. Hydroboration is more facile than hydroalumination, and proceeds by cis addition to the double bond. Cis addition of R2AI—H to the double bond may reasonably be presumed but is not definitely established, since there is no test of cis addition for the terminal olefins which are most commonly subjected to hydroalumination. 

Instead of MesAl, DIBAH-derived alkylaluminums via hydroalumination of alkenes were also applicable (Equation 60) [68]. 1-Decene is converted into n-decylaluminum (142) and subjected to ZACA reaction in the presence of isobuty-laluminum oxide (IBAO) to afford the corresponding optically active compound (143). 

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