132380-31-5Relevant academic research and scientific papers
Organoboranes. 54. Exploration of the reactions of (α-haloallyl)lithium with organoborane derivatives. Simple and convenient procedure for the synthesis of three-carbon homologated boronate esters and terminal alkenes
Brown, Herbert C.,Rangaishenvi, Milind V.,Jayaraman, Seetharaman
, p. 1948 - 1954 (2008/10/08)
The synthetic utility of (α-haloallyl)lithium generated in situ for the facile transfer reaction of various organoborane derivatives, such as R3B, R2BOR′, and RB(OR′)2, has been explored. This has led to the synthesis of α-vinylboronate esters, RCH(CH=CH2)B(OR′)2. which are readily isomerized thermally to the corresponding allylboronate esters with the boron atom on the less substituted carbon atom, RCH= CHCH2B(OR′)2. Catalytic hydrogenation of these allylboronate esters furnishes saturated boronate esters, RCH2CH2CH2B(OR′)2, providing a three-carbon homologation of the original R-B2CH=CH2.
