Preparation of Poly(Ethylene Glycol) Sulfonamide:Synthesis of N-Supported beta-Aminoesters via the Aza-Baylis-Hillman Reaction

摘要

The 2-trimethyl silyl ethylsulfonyl (or SES) group is a valuable protecting group of amines in organic synthesis.It can be cleaved by fluoride-promoted beta-elimination.The SES-activated imines generated either from the corresponding sulfinyl chloride,SES-NH_2~3 or from SES-NSO~4 are promising synthetic intermediates,since they can be involved in various reactions for the construction of more complex molecules,such as Diels-Alder~(4a,5) or [3 + 2] cycloadditions,~(3b) aziridination,~(3a,b) reduction,~(4c,7) and addition of organo-metallics~(4b,d,8) or enol ethers.~(3c,9).