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Practical methodology for the bis-O-methylation of (3S)-isopropyl-piperazine-2,5-dione 4 on a 45 g scale to generate Schollkopf's bis-lactim ether chiral auxiliary (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine 1 has been developed. Monomethylated intermediates 5 and 6 are reported for the first time. The gelling effects of 4 in a range of common solvents are also described.

Original publication

DOI

10.1016/S0957-4166(97)00623-X

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

30/01/1998

Volume

9

Pages

321 - 327