Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters catalyzed by a beta-sulfonamide alcohol.
This work concerns the asymmetric addition of methyl propiolate to aldehydes with 1,2-dimethoxyethane (DME) as additive and beta-sulfonamide alcohol titanium complex as a catalyst. The reactions proceeded under mild conditions and gave the highly functionalized chiral propargylic alcohols with high ee values and good yields. Differences between three types of ligands have also been discussed.
Lin
Li
L
State Key Laboratory of Applied Organic Chemistry, Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, China.
Jiang
Xianxing
X
Liu
Weixia
W
Qiu
Li
L
Xu
Zhaoqing
Z
Xu
Jiangke
J
Chan
Albert S C
AS
Wang
Rui
R
D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
D000438:Alcohols; D000480:Alkynes; D004952:Esters; D009942:Organometallic Compounds; D013449:Sulfonamides; D014025:Titanium