Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent

Lipase-Mediated Resolution of 4-TMS-3-butyn-2-ol and Use of the Mesylate Derivatives as a Precursor to a Highly Stereoselective Chiral Allenylindium Reagent

An improved procedure for the resolution of 4-trimethylsilyl-3-butyn-2-ol has been developed. The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.

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Veröffentlicht in:Organic letters 2001-10, Vol.3 (21), p.3369-3372
Hauptverfasser: Marshall, James A, Chobanian, Harry R, Yanik, Mathew M
Format: Artikel
Sprache:eng
Schlagworte:
Acetylation
Alkynes - chemistry
Butanols - chemistry
Chromatography, Liquid - methods
Indicators and Reagents
Lipase - metabolism
Lipase - pharmacology
Mesylates - chemistry
Methods
Propanols - chemistry
Stereoisomerism
Trimethylsilyl Compounds - chemistry
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Zusammenfassung:An improved procedure for the resolution of 4-trimethylsilyl-3-butyn-2-ol has been developed. The mesylate derivatives of the resolved alcohols have been found to undergo highly enantio-, regio-, and diastereoselective additions to aldehydes, leading to homopropargylic alcohol adducts.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016605x