An improved synthesis of deuterated Schollkopf's bis-lactim ether and its use for the asymmetric synthesis of (R)-[alpha-H-2]-phenylalanine methyl esters

P J M Taylor, S D Bull

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15 Citations (Scopus)

Abstract

Treatment of (S)-3-isopropyl-2,5-dimethoxy-3,6-dihydropyrazine with trifluoroacetic acid in MeOD results in regioselective deuteration at its C-6-position affording its corresponding (S)-[6-H-2(2)]-isotopomer in excellent yield with no loss of stereochemical integrity at its C-3-stereocentre. The lithium aza-enolate of this deuterated chiral template has been alkylated with a range of substituted benzyl bromides to afford (3S,6R)-[6-H-2]-3-isopropyl-6-benzyl-bis-lactim ethers that were hydrolysed to afford their corresponding (R)-[alpha-H-2]-phenylalanine methyl esters as hydrochloride salts in good yield. (c) 2006 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1170-1178
Number of pages9
JournalTetrahedron: Asymmetry
Volume17
Issue number8
DOIs
Publication statusPublished - 2006

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