124937-53-7Relevant articles and documents
Asymmetric Hydroesterification of Diarylmethyl Carbinols
Tian, Duanshuai,Xu, Ronghua,Zhu, Jinbin,Huang, Jianxun,Dong, Wei,Claverie, Jerome,Tang, Wenjun
supporting information, p. 6305 - 6309 (2021/02/09)
An efficient asymmetric hydroesterfication of diarylmethyl carbinols is developed for the first time with a Pd-WingPhos catalyst, resulting in a series of chiral 4-aryl-3,4-dihydrocoumarins in excellent enantioselectivities and good yields. The method features mild reaction conditions, a broad substrate scope, use of easily accessible starting materials, and low palladium loadings. A plausible stereochemical model is also proposed with the Pd-WingPhos catalyst. This method has enabled a 4-step asymmetric synthesis of (R)-tolterodine from readily available starting materials.
Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides
Fernandes, Rodney A.,Gangani, Ashvin J.,Kunkalkar, Rupesh A.
, p. 3970 - 3984 (2020/03/19)
An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.
Synthesis method of tolterodine and enantiomers thereof
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Paragraph 0086-0099, (2019/10/01)
Belonging to the field of chemical synthesis, the invention discloses a synthesis method of tolterodine and enantiomers thereof. The method includes: taking cinnamaldehyde as the raw material for asymmetric arylation reaction with (2-hydroxy-5-methylphenyl)boric acid under the action of a rhodium catalyst to obtain a hemiacetal intermediate, and subjecting the hemiacetal intermediate directly to reductive amination reaction without purification, thus obtaining high optically pure tolterodine. 2-hydroxyl-5-methyl cinnamaldehyde and phenylboronic acid are taken as the starting raw materials, andthe same synthesis method and operation steps are employed to prepare high optically pure tolterodine enantiomers. The method reported by the invention has the characteristics of short route, high total yield, good stereoselectivity and the like, and the ee values of the two synthesized configuration products are both greater than 99%.
