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Authors
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Zimmer, R. ; Ziemer, A. ; Gruner, M. ; Brudgam, I. ; Hartl, H. ; Reissig, H. U.
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Title
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Siloxycylopropanes in ugi four-component reaction: a new method for the synthesis of highly substituted pyrrolidinone derivatives
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Date
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31.12.2001
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Number
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38004
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Abstract
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Reaction of methyl trimethylsiloxycyclopropanecarboxylates 3 with amino acids, tert-butylisonitrile and methanol furnished amino diacid derivatives 2 as the result of an Ugi 5-center 4-component reaction. This one-pot reaction involves ß-formyl esters such as 1 as intermediate, which are liberated in situ. Adducts 2 could be thermally cyclized to provide ·-lactams 4 in good yields. The multi component reaction was combined with this cyclization process to a fairly efficient one-pot procedure. Thus, cyclopropane derivative 3a was converted into ·-lactam 4a in good yield. Two of the ·-lactams 4 were reduced with lithium aluminum hydride to give pyrrolidine derivatives 5. Based on an X-ray analysis of the major diastereomer of compound 5d, the diastereoselectivity of the 4-component reaction is discussed.
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Publisher
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Synthesis - Stuttgart
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Wikidata
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Citation
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Synthesis - Stuttgart (2001) 1649-1658
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DOI
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https://doi.org/10.1055/s-2001-16762
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Tags
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