168051-58-9Relevant academic research and scientific papers
Highly enantioselective catalytic alkyl propiolate addition to aliphatic aldehydes
Turlington, Mark,DeBerardinis, Albert M.,Pu, Lin
supporting information; experimental part, p. 2441 - 2444 (2009/11/30)
A novel H8BINOL-based chiral ligand (S)-3 is found to catalyze the alkyl propiolate addition to aliphatic aldehydes in the presence of ZnEt2 and Ti(OiPr)4 at room temperature with excellent enantioselectivity (89-97% ee).
3,3′-anisyl-substituted BINOL, H4BINOL, and H 8BINOL ligands: Asymmetric synthesis of diverse propargylic alcohols and their ring-closing metathesis to chiral cycloalkenes
Yue, Yang,Turlington, Mark,Yu, Xiao-Qi,Pu, Lin
supporting information; experimental part, p. 8681 - 8689 (2009/12/30)
(Chemical Equation Presented) A series of optically active BINOL, H 4BINOL, and H8BINOL derivatives were prepared. These compounds in combination with ZnEt2 and Ti(OiPr) 4 were used to catalyze the asymmetric reaction of alkynes with aldehydes to generate chiral propargylic alcohols at room temperature. Through this comparative study, a 3,3′-bisanisyl-substituted H8BINOL (S)-7 was found to be a generally enantioselective catalyst for the reaction of structurally diverse terminal alkynes with a variety of aldehydes. It catalyzed the reactions of alkyl propiolates with 88-99% ee; the reactions of phenylacetylene with 81-87% ee; the reactions of 4-phenyl-1-butyne, an alkyl alkyne, with 77-89% ee; and the reactions of trimethylsilylacetylene with 92-97% ee. The optically active propargylic alcohols generated from this catalytic asymmetric alkyne addition were observed to undergo efficient ring-closing-metathesis (RCM) reaction in the presence of the Grubbs II catalyst to produce chiral cycloalkenes. It was further found that some of the chiral propargylic alcohols underwent a highly chemoselective tandem RCM hydrogenation reaction with retention of the enantiomeric purity. 2009 American Chemical Society.
LIGANDS FOR ALDOKETOREDUCTASES
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Page/Page column 164-165, (2008/06/13)
The present invention relates to compounds useful for detecting the activity of human aldoketoreductase 1Cs, compounds useful for competitively inhibiting human aldoketoreductase 1Cs and compounds useful for treating human aldoketoreductase 1C-related can
A mild method for the preparation of γ-hydroxy-α,β- acetylenic esters
Shahi, Shatrughan P.,Koide, Kazunori
, p. 2525 - 2527 (2007/10/03)
The beauty of silver has been demonstrated in the alkynylation of functionalized aldehydes and ketones. Silver acetylides of alkynyl propiolates undergo addition to carbonyl compounds in the presence of [Cp 2ZrCl2] and AgOTf (see scheme) in a reaction that is compatible with both base-sensitive and acid-sensitive functional groups. Tf = trifluoromethanesulfonyl.
