113163-08-9Relevant academic research and scientific papers
Chiral Synthesis via Organoboranes. 17. Preparation of α-Chiral α'-Alkynyl Ketones of High Enantiomeric Excess from Optically Pure Organyl(1-alkynyl)borinic Esters
Brown, Herbert C.,Gupta, Ashok K.,Prasad, Vara J. V. N.,Srebnik, Morris
, p. 1391 - 1394 (1988)
Optically pure alkynylborinic esters R*BCCR''(OR') are cleanly obtained from optically pure boronic esters R*B(OR')2 and a lithium acetylide followed by treatment of the "ate" complex LiR*BCCR''(OR')2 with ethereal hydrogen chloride.These borinic esters react with α,α-dichloromethyl methyl ether, DCME, in the presence of a hindered base to yield, after hydrogen peroxide oxidation, α-chiral α'-alkynyl ketones R*COCCR'' which exhibit the same high enantio- and stereoselectivity of the chiral boronic esters. β-Heterosubstituted (1-alkynyl)borinic esters, such as , despite their sensitivity to elimination reactions, can be similarly converted into the corresponding ketones in excellent yields.This development considerably expands the range of applicability of the "DCME" reaction.
