A new class of ligands for aqueous, lanthanide-catalyzed, enantioselective Mukaiyama aldol reactions.
The development of aqueous methods for generating enantiopure β-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral β-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded β-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively.
Mei
Yujiang
Y
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.
Dissanayake
Prabani
P
Allen
Matthew J
MJ
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D028581:Lanthanoid Series Elements / Q000737:chemistry*; D008024:Ligands; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D028581:Lanthanoid Series Elements; D008024:Ligands; D009942:Organometallic Compounds; D014867:Water; C116609:3-hydroxybutanal
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