83681-58-7Relevant academic research and scientific papers
ORGANOBORANES-34; GENERAL SYNTHESIS OF CHIRAL BORONIC AND BORINIC ESTERS VIA ASYMMETRIC HYDROBORATION-DISPLACEMENT. CARBENOIDATION OF CHIRAL BORINIC ESTERS TO ACYCLIC KETONES OF HIGH ENANTIMERIC PURITIES
Brown, Herbert C.,Jadhav, Prabhakar K.,Desai, Manoj C.
, p. 1325 - 1332 (2007/10/02)
Asymmetric hydroboration of appropriate alkenes with diisopinocampheylborane (Ipc2BH) or monoisocampheylborane (IpcBH2) produces intermediates that readily eliminate α-pinene on treatment with acetaldehyde, providing a direct, convenient route to chiral boronic esters of high enantiomeric purities.Mixed chiral trialkylboranes, readily prepared by stepwise hydroboration of appropriate alkenes with IpcBH2, eliminate α-pinene on treatment with acetaldehyde under very mild conditions.The procedure makes readily available chiral borinic esters of high enantiomeric purities.The synthetic utility of chiral borinic esters is demonstrated by converting them into acyclic ketones including an alarm pheromone of the ant Manica mutica.
