Palladium-Catalyzed Rearrangement of Allylic Sulfoximines:  Application to the Asymmetric Synthesis of Chiral Allylic Amines

The palladium(0)-catalyzed reactions of the primary and secondary allylic sulfoximines 7, 9, 11, 13, 15, 17, and 19 gives allylic sulfinamides without 1,3-allylic rearrangement. These compounds were not isolated but were converted to their corresponding N-tosyl allylic amines, primary and secondary...

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Published inJournal of organic chemistry Vol. 61; no. 16; pp. 5517 - 5522
Main Authors Pyne, Stephen G, Dong, Zemin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.08.1996
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUTION
KETONES
REAGENTS
SULFUR-COMPOUNDS
SULFINAMIDE REARRANGEMENT
NUCLEOPHILIC ALKYLIDENE TRANSFER
CONJUGATE
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Summary:The palladium(0)-catalyzed reactions of the primary and secondary allylic sulfoximines 7, 9, 11, 13, 15, 17, and 19 gives allylic sulfinamides without 1,3-allylic rearrangement. These compounds were not isolated but were converted to their corresponding N-tosyl allylic amines, primary and secondary 8, 10, 12, 14, 16, 18, and 20, respectively. In the case of the optically active secondary allylic sulfoximines 17 and 19, chiral N-tosyl allylic secondary amines were formed in high enantiomeric purities.
Bibliography:istex:6006767E10963E22F1A64B633BE4A27622D81697
Abstract published in Advance ACS Abstracts, July 15, 1996.
ark:/67375/TPS-TJ73J1PR-S
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9605105