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Catalytic, Asymmetric Synthesis of Phosphonic γ‐(Hydroxyalkyl)butenolides with Contiguous Quaternary and Tertiary Stereogenic Centers
Author(s) -
Frings Marcus,
Thomé Isabelle,
Schiffers Ingo,
Pan Fangfang,
Bolm Carsten
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304331
Subject(s) - stereocenter , enantiopure drug , nucleophile , electrophile , chemistry , aldol reaction , enantioselective synthesis , catalysis , stereochemistry , combinatorial chemistry , organic chemistry
A procedure that enables high yielding access to phosphonic γ‐(hydroxyalkyl)butenolides with excellent regio‐, diastereo‐ and enantiocontrol is reported. The simultaneous construction of up to two adjacent quaternary stereogenic centers by a catalytic asymmetric vinylogous Mukaiyama aldol reaction unites biologically and medicinally relevant entities, namely α‐hydroxy phosphonates and γ‐(hydroxyalkyl)butenolides. This is achieved by utilizing a readily available chiral copper‐sulfoximine catalyst showing a broad functional group tolerance for both the electrophilic and nucleophilic reactants. A discussion about potential factors affecting the observed level of enantioselectivity, which stems from the enantiopure sulfoximine ligand, is also included.