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New Applications of N ‐Acyliminium Precursors: Tetracarbonyliron‐Mediated Stereoselective Alkylations of 5‐( R )‐Isopropoxy‐3‐pyrrolin‐2‐ones
Author(s) -
de Koning Henk,
Hiemstra Henk,
Moolenaar Marinus J.,
Speckamp W. Nico
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199809)1998:9<1729::aid-ejoc1729>3.0.co;2-o
Subject(s) - chemistry , stereoselectivity , allylic rearrangement , nucleophile , lewis acids and bases , tosyl , medicinal chemistry , stereochemistry , catalysis , organic chemistry
Lewis acid catalyzed allylic substitutions with several nucleophiles at C‐5 of the cis ‐tetracarbonyliron complexes of N ‐acetyl‐ and N ‐tosyl‐5‐( R )‐isopropoxy‐3‐pyrrolin‐2‐ones occur highly regio‐ and stereoselectively. The results are interpreted as being indicative of the intermediacy of a (π‐allyl)tetracarbonyliron cation, with possible preceding formation of an N ‐acyl‐ or an N ‐tosyliminium ion.