3-Hydroxypyrrolidines from epoxysulfonamides and dimethylsulfoxonium methylide

Abstract

N-Tosyl-protected 3-hydroxypyrrolidines are prepared by reaction of dimethylsulfoxonium methylide with readily available epoxysulfonamides.

Silicon assisted diversified reaction of a β-silylmethylene malonate with dimethylsulfoxonium methylide

“…In separate experiments, cyclopropane 3a was found to be unreactive to the ylide 5 even when treated in large excess. Although, cyclopropanes are known not to react with excess DIM-SOY to give cyclobutanes, DIMSOY can add to epoxides and suitably N-protected aziridines under harsh conditions to give oxetanes [64][65][66][67][68] and azetidines [69,70] or other products [71][72][73][74][75][76], depending on the other functionalities present on the substrates. A plausible mechanism for the formation of cyclobutane products from silyl substituted methylene malonates 2 is delineated in Scheme 7.…”

Microbial Transformation of Nitrogen Containing Heterocycles

“…Some stereoisomers of 2-(hydroxymethyl)pyrrolidine-3,4-diols also have been reported as glycosidase inhibitors (Ahn and Shin 1997). The 3hydroxypyrrolidine moiety is found in a range of naturally occurring bioactive alkaloids and many synthetic approaches to produce 3-hydroxypyrrolidines also have been developed (Aurrecoechea et al 2009;Hodgson et al 2006;Rios et al 2007).…”

Heterocyclic chemistry

“…25 All of these are shown in Scheme 21. Hodgson has reported an interesting 3-hydroxypyrrolidine synthesis using a sulfur ylide ring-opening of an a-amino epoxide, 26 which generates an alkoxide ion that removes a proton from the vicinal sulfonamide, followed by an intramolecular displacement of the sulfoxonium group by the sulfonamide anion, giving the hydroxypyrrolidine products in excellent yields and with high levels of stereocontrol (Scheme 22). An additional interesting point to the synthesis is that the epoxide starting materials themselves can be synthesised through sulfur ylide addition.…”