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Remarkable Dependence of Diastereoselectivity on Anhydrous or Aqueous Solvent in the Indium Hydride Promoted Reductive Aldol Reaction of α,β‐Unsaturated Ketones
Author(s) -
Inoue Katsuyuki,
Ishida Tatsuya,
Shibata Ikuya,
Baba Akio
Publication year - 2002
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 - 10.1002/1615-4169(200206)344:3/4<283::aid-adsc283>3.0.co;2-s
Subject(s) - chemistry , aldol reaction , anhydrous , hydride , tributyltin hydride , selectivity , solvent , organic chemistry , transmetalation , methanol , indium , dichloromethane , medicinal chemistry , catalysis , hydrogen
Dichloroindium hydride generated by the transmetallation between tributyltin hydride and indium trichloride predominantly reduced α,β‐unsaturated ketones (enones) with 1,4‐selectively even in the presence of aldehydes. Under anhydrous conditions, the successive aldol reaction between the resulting enolates and the remaining aldehydes proceeded with high anti ‐selectivity. The stereochemistry was dramatically reversed to be syn ‐selective by the use of water and methanol as an additive and solvent, respectively.