The first synthesis of N,O-protected β^2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams

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• 作者：Andrea Guerrini ; Greta Varchi ; Cristian Samorì ; Rizzo Daniele ; Battaglia Arturo
• 关键词：Tetrasubstituted β ; ² ; 2 ; 3 ; 3-isoserines ; Tetrasubstituted 3-hydroxy-β ; -lactams ; β ; -Peptides ; α ; -Hydroxy-β ; -amino acids
• 刊名：Tetrahedron Letters
• 出版年：2007
• 出版时间：16 July 2007
• 年：2007
• 卷：48
• 期：29
• 页码：5081-5085
• 全文大小：165 K

文摘

The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (S_R)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformationally restrained β^2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1′-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1′-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-β-lactams. The synthesis of a dipeptide by reaction coupling between the 1′-aminodioxolanone (2S,5R,1′R)-19 and N,N-dimethylglycine was successfully achieved.