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

Autor:	W. Nico Speckamp, Henk Hiemstra, Wim J. Klaver
Rok vydání:	1987
Předmět:	Bicyclic molecule Formic acid Organic Chemistry Alkylation Biochemistry chemistry.chemical_compound Deprotonation chemistry Drug Discovery Alkoxy group Lactam Acetone Organic chemistry Isopropyl
Zdroj:	Tetrahedron Letters. 28:1581-1584
ISSN:	0040-4039
Popis:	The alkylation of the dianion of the title compound ( 2 ) readily prepared from (S)-malic acid, with ω-iodo-1-trimethylsilyl-2-alkynes ( 8a - c ) occurs with high trans-selectivity with respect to the hydroxyl function. The products ( 11a - c ) cyclize in formic acid to enantiomerically pure azabicyclic allenes ( 12a - c ), one of which ( 12b ) might be a suitable precursor to peduncularine ( 15 ).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a2fed396d9ed8e0cd20d9d11c216a8ff https://doi.org/10.1016/s0040-4039(01)81047-9 Zobrazit plný text záznamu