95535-40-3Relevant articles and documents
Solid phase synthesis of bicyclic pyrrolidines
Quadrelli, Paolo
, (2021/11/17)
The preparation of bicyclic pyrrolidines, stable and easy to isolate, is performed through both classical solution chemistry and on solid support. A new linker strategy is presented based on the concept of REM resin approach. Starting from a suitably derivatized Wang's resin, the linker can be REgenerated after cleavage of the product and functionalized to start a new synthetic cycle via a Michael reaction. In the present work a vinyl sulfone supported on a Wang's resin is able to undergo a Michael reaction with an amino acid derivative; the obtained adduct serves as a precursor for azomethine ylide generation, which is conveniently trapped with N-methyl-maleimide. The results are presented and discussed in the light of the experimental conditions applied as well as the method chosen for the cleavage of the product and resin regeneration.
Fluorescent and Nonfluorescent Aryl Vinyl Sulfones - Reagents Suitable for Protection and Detection of Thiol Functions
Horner, Leopold,Lindel, Hans
, p. 22 - 33 (2007/10/02)
The rate of the addition of primary, secondary, and tertiary thiols to aryl/alkyl vinyl sulfones 1 and 4-7 is investigated by competing reactions and by kinetics.The obtained acid stable 2-(alkyl-/arylthio)ethyl sulfones are cleaved by bases to give the starting material by rates corresponding to the rates of addition.Therefore, selective introduction and selective elimination of different (arylsulfonyl)ethyl protective groups in the same molecule is possible by using different kinetic steering factors. - Application of the fluorescent vinyl sulfones 5, 10, and 11 opens new fields for analysis and synthesis.SH-selective vinyl sulfones and thiophosphinic acid cyanides are "orthogonal" protective groups.