Synthesis of β-methyl-β-alanine-l-proline-XAA tripeptides by Yb(OTf)3 catalysed Michael addition of amines to N-crotonyl-l-proline-XAA: a versatile route to cyclic β-methyl-β-alanine-derived tripeptides via ring closing metathesis

doi:10.1016/S0040-4039(02)01237-6

Tetrahedron Letters

Volume 43, Issue 36, 2 September 2002, Pages 6467-6471

https://doi.org/10.1016/S0040-4039(02)01237-6 Get rights and content

Abstract

N-Crotonyl-l-proline derived peptides can be transformed to the corresponding β-methyl-β-alanine-l-proline peptides by Yb(OTf)₃ catalysed Michael addition of aliphatic amines to the crotonyl residue. The Michael adducts derived from addition of allylamine are versatile precursors to the corresponding cyclic peptides obtainable via ring closing metathesis.

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Synthesis of β-methyl-β-alanine-l-proline-XAA tripeptides by Yb(OTf)3 catalysed Michael addition of amines to N-crotonyl-l-proline-XAA: a versatile route to cyclic β-methyl-β-alanine-derived tripeptides via ring closing metathesis

Abstract

Acc. Chem. Res.

J. Chem. Soc., Perkin Trans. 1

Eur. J. Org. Chem.

Enantioselective Synthesis of β-Amino Acids

Angew. Chem., Int. Ed. Engl.

Helv. Chim. Acta

Acc. Chem. Res.

J. Am. Chem. Soc.

Tetrahedron Lett.

Chem. Rev.

Biochemistry

AIDS Res. Human Retroviruses

J. Am. Chem. Soc.

Med. Res. Rev.

Biochem. Biophys. Res. Commun.

Chem. Lett.

Tetrahedron Lett.

Synthesis of β-methyl-β-alanine-l-proline-XAA tripeptides by Yb(OTf)₃ catalysed Michael addition of amines to N-crotonyl-l-proline-XAA: a versatile route to cyclic β-methyl-β-alanine-derived tripeptides via ring closing metathesis