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Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid Derived N-Acyliminium Ions (1999)

Rutjes, Floris P. J. T. ; Veerman, Johan J. N. ; Meester, Wim J. N. ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 1127-1135

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ISSN: 1434-193X

Keywords: Non-natural amino acids ; N-Acyliminium ions ; Enzymatic resolution ; Pipecolic acid derivatives ; Rearrangements ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: -The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

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