Aza-Baylis–Hillman reaction
Aza-Baylis-Hillman reaction | |
---|---|
Named after | Anthony B. Baylis Melville E. D. Hillman |
Reaction type | Coupling reaction |
Identifiers | |
RSC ontology ID | RXNO:0000264 |
The aza-Baylis–Hillman reaction or aza-BH reaction in
BINOL and phosphinyl BINOL compounds,[1] for example in the reaction of n-(4-chloro-benzylidene)-benzenesulfonamide with methyl vinyl ketone (MVK) in cyclopentyl methyl ether and toluene
at -15°C.
In one study a
racemisation
process simply by mixing chiral aza-BH adduct, phosphine and acid.
Asymmetric aza-BH
Aza-BH reactions are known in
chiral ligands. In one study,[3] for the first time, successful use was made of a chiral solvent based on an ionic liquid
(IL).
This solvent is a condensation product of L-(−)-
ammonium salt the resulting ionic liquid has a melting point
of −32°C.
This IL serves as the chiral solvent for the aza-BH reaction between N-(4-bromobenzylidene)-4-toluenesulfonamide and
chemical yield 34–39% and enantiomeric excess
71–84%.
References
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- Angewandte Chemie International Edition volume 45, Issue 22 , Pages 3689 - 3692 2006 Abstract