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Synthesis of Chiral Vinylogous Sulfonamidopeptides (vs-Peptides)

✍ Scribed by Cesare Gennari; Chiara Longari; Stefano Ressel; Barbara Salom; Antonia Mielgo

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
665 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

Chiral vinylogous amino sulfonic acids (vs-amino acids) were synthesized starting from either L-or D-Ξ±-amino acids via N-BocΟͺΞ±-amino aldehydes. Wittig-Horner reaction with methyl (or ethyl) diethylphosphoryl methanesulfonate and nBuLi gave the corresponding Ξ±,Ξ²-unsaturated sulfonates in high yield and complete (E) stereoselectivity. Cleavage of the methyl (ethyl) ester was effected by treatment of the sulfonates with nBu 4 NI in refluxing acetone. Treatment of the nBu 4 N + sulfonate salts with SO 2 Cl 2 /PPh 3 /CH 2 Cl 2 gave the corresponding sulfonyl chlorides as stable chromatographable compounds. The synthetic sequence proved successful not only starting from Ξ±-amino acids carrying

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