Readily available sulfamide-amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(O(i)Pr)4.
Ephedrine-derived sulfamide-amine alcohol 3 was found to be an effective catalyst for the asymmetric phenylacetylene addition to aldehydes at room temperature without using Ti(O(i)Pr)4 and Zn(OTf)2. It afforded the propargylic alcohols in high yields (up to 99%) and good enantioselectivities (up to 84% ee), which were much higher than that based on N-methylephedrine under the same reaction conditions. Its weakly coordinative sulfonamide moiety of the ligand plays an important role for further acceleration and stereocontrol in the alkynylation.
Mao
Jincheng
J
Dalian Institute of Chemical Physics, Graduate School of Chinese Academy of Sciences, Dalian 116023, China.
Wan
Boshun
B
Wu
Fan
F
Lu
Shiwei
S
D000114:Acetylene / Q000031:analogs & derivatives* / Q000494:pharmacology*; D000438:Alcohols / Q000737:chemistry / Q000494:pharmacology*; D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004583:Electrons; D008024:Ligands; D008956:Models, Chemical; D009942:Organometallic Compounds; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013696:Temperature; D014025:Titanium / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
D000438:Alcohols; D000447:Aldehydes; D000588:Amines; D008024:Ligands; D009942:Organometallic Compounds; D013449:Sulfonamides; C044736:phenylacetylene; C102815:titanium isopropoxide; D014025:Titanium; D015032:Zinc; D000114:Acetylene