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- Title
Catalytic, Asymmetric Synthesis of Phosphonic γ-(Hydroxyalkyl)butenolides with Contiguous Quaternary and Tertiary Stereogenic Centers.
- Authors
Frings, Marcus; Thomé, Isabelle; Schiffers, Ingo; Pan, Fangfang; Bolm, Carsten
- Abstract
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.
- Subjects
BUTENOLIDES synthesis; PHOSPHONATES; ORGANIC synthesis; ASYMMETRIC synthesis; SULFOXIMINES; ELECTROPHILIC addition reactions; NUCLEOPHILIC reactions
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 6, p1691
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201304331