Asymmetric addition of phenylacetylene to aromatic ketones catalyzed by zinc or titanium complexes with chiral hydroxysulfonamide.
Various new chiral hydroxysulfonamide ligands (3a-3n, 4a-4d) were prepared. Compounds 3a, 3g, 3i, 3k-3n, 4a-4d could accelerate the reaction and reduce reaction time, and 3a, 3g, 3i, 3k-3n catalyzed the reaction without titanium. The results obtained were promising in terms of yields and enantiomeric excesses (3k up to 85% ee, 4a up to 83% ee).
Zhou
Yi-Feng
YF
College of Life Sciences, China Jiliang University, Hangzhou, China.
Han
Zhi-Jian
ZJ
Qiu
Li
L
Liang
Jin-Yan
JY
Ren
Feng-Bo
FB
Wang
Rui
R
D000098:Acetophenones / Q000737:chemistry; D000114:Acetylene / Q000031:analogs & derivatives* / Q000494:pharmacology; D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007659:Ketones / Q000378:metabolism*; D008024:Ligands; D008956:Models, Chemical; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013696:Temperature; D013997:Time Factors; D014025:Titanium / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D000098:Acetophenones; D000438:Alcohols; D007659:Ketones; D008024:Ligands; D013449:Sulfonamides; C044736:phenylacetylene; D014025:Titanium; D015032:Zinc; D000114:Acetylene; C038699:acetophenone