Camphor reaction with lithium aluminum hydride

The authors provided some experimental support for their hypothesis by performing various diastereoselective reactions on racemic or optically active compounds. Indeed, they found some differences in stereoselectivity between the two cases. Reduction of DL-camphor or D-camphor with lithium aluminum hydride, for example, gave ratios of isobomeol to bomeol of 7.93 and 9.20, respectively. 

In 1951 Bothner-By first attempted asymmetric reductions based on the conversion of lithium aluminum hydride (LAH) into a chiral alkoxy derivative by reaction with (+)-camphor. Since this pioneering work, the use of chirally modified LAH reagents has been the focus of much attention. In 1979, the first virtually complete enantiofacial recognition of prochiral carbonyl compounds was accomplished by using LAH modified with optically pure 2,2 -dihydroxy-1,1 -binaphthyl and a simple alcohol (BINAL-H). Asymmetric reduction with chiral 2,5-dimethylborolane also gave alcohols in high optical yields." Recently, excellent results have been obtained using a chirally modified sodium borohydride... 

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