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Diastereoselective alkylation of the dianion of 5-ethoxy-4(S)-hydroxy-1-isopropyl-2-pyrrolidinone; Synthesis of enantiomerically pure azabicycles

โœ Scribed by Wim J. Klaver; Henk Hiemstra; W.Nico Speckamp


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
281 KB
Volume
28
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The alkylation of the dianion of the title compound (2), readily prepared from (S)malic acid, with w-iodo-l-trimethylsilyl-2-alkynes (8a-c) occurs with high trans-selectivity with respect to the hydroxyl function. The productsTITa-c) cyclize in formic acid to enantiomerically pure azabicyclic allenes (12a-c), one of wah-(12b) might be a suitable precursor to peduncularine (15).


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