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Diversity‐Oriented Preparation of Enantiopure Spirocyclic 2‐Azetidinones from α‐Oxo‐β‐lactams through Barbier‐Type Reactions followed by Metal‐Catalyzed Cyclizations
Author(s) -
Alcaide Benito,
Almendros Pedro,
del Campo Teresa Martínez,
RodríguezAcebes Raquel
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600502
Subject(s) - enantiopure drug , chemistry , catalysis , regioselectivity , reagent , alcohol , palladium , organic chemistry , azetidine , ruthenium , combinatorial chemistry , enantioselective synthesis
Novel, simple, and convenient strategies to diversely functionalized spirocyclic β‐lactams have been developed by using different metal‐mediated carbonyl addition/cyclization reaction sequences. Spirocyclization precursors, 2‐azetidinone‐tethered homoallylic alcohols, bromohomoallylic alcohols, homopropargylic alcohols, (buta‐1,3‐dien‐2‐yl)methanols, and α‐allenols have been obtained by regioselective addition of stabilized organometallic reagents to azetidine‐2,3‐diones in an aqueous environment. Ruthenium‐, silver‐, and palladium‐catalyzed reactions of the above monocyclic unsaturated alcohol derivatives provided oxaspiro‐β‐lactams.