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B.R.S.M — An organic chemistry blog

Sucralose - Wikipedia

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"The result of initial synthetic efforts involving model systems led us to conclude that construction of such systems would have to take into account the unique behaviour and properties of a polychlorinated backbone with electron-withdrawing groups. As a relevant benchmark, sucralose, the key ingredient of Splenda, incorporates two 1° and one 2° chlorides on a disaccharide core and is sufficiently stable and safe to be widely used as an artificial sweetener. In a similar fashion, in preliminary investigations we observed that displacement reactions of activated alcohol derivatives to furnish the corresponding alkyl chlorides proved unworkable when the carbinol bears two methine substituents with electron-withdrawing groups, such as chlorides. Additionally, we noted that α- and β-chlorinated aldehydes are fleeting intermediates, which undergo enolization, hydration or elimination too rapidly. Thus, we sought to implement strategic approaches that would circumvent these limitations in crafting a synthesis route to chlorosulpholipid 5." - Carreira in

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Anyway, that’s probably enough pontification for one blog post, so here are a few of my favourite syntheses and a few that came up in recent conversations—please add yours and your thoughts in the comments!

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Acknowledgement: I took the term 'Splenda Effect' from Carreira's talk at the Bristol Synthesis Meeting on Tuesday. It's a useful term to describe the low reactivity of alkyl halides near electron withdrawing groups. This post is mostly sourced from that, wikipedia and the Nature paper cited below.

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