We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Asymmetric Synthesis of α-Substituted N-Methylsulfonamides.
- Authors
Enders, Dieter; Thomas, Christian R.; Vignola, Nicola; Raabe, Gerhard
- Abstract
A novel amine auxiliary for the asymmetric synthesis of α-substituted N-methylsulfonamides is described. The reaction of 4-([1,1′-biphenyl]-4-yl)-2,2-dimethyl-1,3-dioxan-5-amine ( 16) with various aliphatic sulfonyl chlorides afforded the corresponding sulfonamides, which were lithiated and subsequently reacted with electrophiles to give the corresponding products in high yields and good-to-excellent asymmetric inductions (de 83-95%). Racemization-free cleavage of the auxiliary led to the α-alkylated N-methylsulfonamides in acceptable yields and high enantiomer purities (ee 91 to ≥98).
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 11, p3657
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/1522-2675(200211)85:11<3657::AID-HLCA3657>3.0.CO;2-A