127180-75-0Relevant articles and documents
Mechanistically Guided Design of an Efficient and Enantioselective Aminocatalytic α-Chlorination of Aldehydes
Hutchinson, George,Alamillo-Ferrer, Carla,Burés, Jordi
supporting information, p. 6805 - 6809 (2021/05/29)
The enantioselective aminocatalytic α-chlorination of aldehydes is a challenging reaction because of its tendency to proceed through neutral intermediates in unselective pathways. Herein we report the rational shift to a highly selective reaction pathway involving charged intermediates using hexafluoroisopropanol as solvent. This change in mechanism has enabled us to match and improve upon the yields and enantioselectivities displayed by previous methods while using cheaper aminocatalysts and chlorinating agents, 80-95% less amount of catalyst, convenient temperatures, and shorter reaction times.
A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides
Reed, Carson W.,Lindsley, Craig W.
supporting information, (2019/09/10)
In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of
Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes
Jimeno, Ciril,Cao, Lidong,Renaud, Philippe
, p. 1251 - 1255 (2016/02/19)
Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.