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The highly diastereoselective samarium diiodide and D(2)O-promoted conjugate reduction of homochiral (E)- and (Z)-benzylidene and isobutylidene diketopiperazines (E)-5,7 and (Z)-6,8 has been demonstrated. This methodology allows the asymmetric synthesis of methyl (2S,3R)-dideuteriophenylalanine 27 in > or = 95% de and >98% ee, and (2S,3R)- or (2S,3S)-dideuterioleucine-(S)-phenylalanine dipeptides 37 and 38 in moderate de, 66% and 74% respectively. A mechanism is proposed to account for this process.

Original publication

DOI

10.1039/b500566c

Type

Journal article

Journal

Org Biomol Chem

Publication Date

21/04/2005

Volume

3

Pages

1435 - 1447

Keywords

Crystallography, X-Ray, Dipeptides, Iodides, Magnetic Resonance Spectroscopy, Molecular Structure, Oxidation-Reduction, Phenylalanine, Samarium, Stereoisomerism