Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step

Dietz FR, Gröger H (2009)
SYNTHESIS-STUTTGART (24): 4208-4218.

Journal Article | Published | English

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An efficient synthetic route to all four stereoisomers of alpha-methylthreonine has been established. Each type of stereoisomer has been isolated in diastereomerically pure form and with an enantiomeric excess of at least 86% ee. The key step in this multi-step synthesis is an enantioselective organocatalytic Steglich rearrangement reaction of O-acetylated azlactones. The Steglich rearrangement was also extended to other substrates.
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Dietz FR, Gröger H. Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step. SYNTHESIS-STUTTGART. 2009;(24):4208-4218.
Dietz, F. R., & Gröger, H. (2009). Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step. SYNTHESIS-STUTTGART(24), 4208-4218.
Dietz, F. R., and Gröger, H. (2009). Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step. SYNTHESIS-STUTTGART, 4208-4218.
Dietz, F.R., & Gröger, H., 2009. Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step. SYNTHESIS-STUTTGART, (24), p 4208-4218.
F.R. Dietz and H. Gröger, “Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step”, SYNTHESIS-STUTTGART, 2009, pp. 4208-4218.
Dietz, F.R., Gröger, H.: Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step. SYNTHESIS-STUTTGART. 4208-4218 (2009).
Dietz, Friedrich R., and Gröger, Harald. “Asymmetric Synthesis of All Stereoisomers of alpha-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step”. SYNTHESIS-STUTTGART 24 (2009): 4208-4218.
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