Reactions with organometallic compounds alcohol synthesis

The reaction of 1-boraadamantane (5) with aromatic nitriles also proceeds according to the organometallic synthesis scheme. As in the reaction with carbonyl compounds, the initially formed complexes (100) (Scheme 37) transform to dimers of 5-aryl-4-aza-3-bora-l,l-bihomoadamantane-4-enes (101) when heated higher than 200 °C <84JOM(260)25>. Compounds (101) are stable in the air and do not react with alcohols however, they can be cleaved with 8-hydroxyquinoline to give bicyclic compounds (102) <84jom(260)25>. 

Synthesis of homoallylic alcohols by the reaction of ally] organometallics with carbonyl compounds is one of the most important processes in organic synthesis... 

A number of highly enantioselective chiral allyl organometallic reagents have been described in the literature. These are of considerable interest both for the asymmetric synthesis of homoallyl alcohols as well as in double asymmetric reactions with chiral C=X electrophiles. - Two distinct groups of chiral allyl metal reagents can be identified those with conventional, easily introduced chiral auxiliaries and ones in which the center of chirality is a structural component of the reagent (e.g. allyl metal compounds with substituents at C-1). These are discussed separately in the sections that follow. 

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