Succinimides, //-substituted, conversion

The succinimide derivative (234) can be used in peptide synthesis for conversion of amino acids into their succinimide esters (235 Scheme 41) (79CL1265). 3-Substituted mercapto-1,2-benzisothiazole 1,1-dioxides (236) have been recommended as an odourless means of storage of thiols. The latter are readily regenerated by the action of piperidine (81CL1457). 

In 2007, Wang and co-workers published a protocol for an enantio- and diastereoselective domino Michael-aldol reaction using electron-rich and electron-deficient 2-mercaptobenzaldehydes and maleimides as substrates [223]. The conversion was described to proceed smoothly in the presence of bifunctional catalyst 12 (lmol% loading) in xylenes at 0°C reaction temperature producing the desired chiral succinimide-containing substituted thiochromanes 1-5 in high yields (83-96%), in synthetically useful ee values (74—94%), and diastereoselectivities (up to dr 20 1) in 7h reaction time (Scheme 6.71). 

An intramolecular cyclization of -hydroxysulfoxides effected by At-chloro-succinimide, A bromosuccinimide, or sulfuryl chloride gives 1,2-oxathietane 2-oxides, for example, 496, via a sulfoxonium salt. These cyclic sulfoxonium intermediates have been suggested in the conversion of /3-hydroxy-sulfoxides to /3-chlorosulfones, and to a,j3-unsaturated sulfones, in the conversion of /3-ethoxycarbonylsulfoxides to alkenes and of /3-hydroxysulfides to /3-hydroxysulfoxides, and in the conversion of 3-hydroxy- 3-vinylsulfoxides (e.g., 497) to useful terpene building blocks. The yields of the products from 497 vary somewhat depending on the stereochemistry about the two chiral centers. The more highly substituted 1,2-oxathietane 2-oxides are the most stable, because of... 

Derivation Conversion of succinic acid to succi-namide, followed by heating ammonia splits off to give a diacyl-substituted derivative (succinimide). 

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