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Cyclic Sulfonimidates by Dynamic Diastereomer‐Differentiating Cyclisation: Large‐Scale Synthesis and Mechanistic Studies
Author(s) -
Reggelin Michael,
Junker Bernd
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010316)7:6<1232::aid-chem1232>3.0.co;2-l
Subject(s) - diastereomer , enantiomer , chemistry , hypochlorite , enantioselective synthesis , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
A dynamic diastereomer differentiating cyclisation is the key step in a new large‐scale synthesis of both enantiomers of the cyclic sulfonimidates 1 (Aldrich no. 54 099‐4) and ent ‐ 1 (Aldrich no. 54 412‐4). These are valuable starting materials in the asymmetric synthesis of chiral oxa‐ and azaheterocyclic compounds. NMR spectroscopic studies on the reacting system reveal N‐chloro sulfinamides to be reactive intermediates in the oxidative chlorination of sulfinamides with tert ‐butyl hypochlorite and allow for the inspection of the configurational behaviour of the involved sulfonimidoyl chlorides and sulfonimidoyl bromides.