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A Method for the Conversion of Sulfoximines to Sulfones: Application to Polymer‐Bound Sulfoximines and to the Synthesis of Chiral Sulfones
Author(s) -
Hachtel Jochen,
Gais HansJoachim
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200004)2000:8<1457::aid-ejoc1457>3.0.co;2-g
Subject(s) - chemistry , sulfone , enantiopure drug , benzaldehyde , yield (engineering) , aryl , alkyl , organic chemistry , deprotonation , cleavage (geology) , enantioselective synthesis , medicinal chemistry , catalysis , ion , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
Reaction of N ‐alkyl, N ‐aryl, and N‐ H sulfoximines with m ‐chloroperbenzoic acid cleanly gives the corresponding sulfones in high yield. In the case of the cleavage of N ‐alkyl and N ‐arylsulfoximines, formation of the corresponding nitroso compounds as the other reaction product was proven. Starting from enantio‐ and diastereopure sulfoximines, a number of chiral sulfones, including the axially chiral sulfone 6 and the sulfonyl‐functionalized homoallylic alcohol 8 , have been prepared. Reaction of the enantiopure sulfoximine 30 with Merrifield resin gave the polymer‐bound sulfoximine 32 . Oxidative cleavage of 32 afforded the sulfone 16 in high yield. Deprotonation of the sulfoximine resin 32 and reaction of Li‐ 32 with benzaldehyde and propanal furnished the β‐hydroxysulfoximine resins 33a and 33b , respectively. Oxidative cleavage of 33a and 33b readily afforded the β‐hydroxy sulfones 14a and 14b , respectively.