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.
[reaction: see text]. 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.
Marshall
J A
JA
Department of Chemistry, University of Virginia, P.O. Box 400319, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Chobanian
H R
HR
Yanik
M M
MM
D000107:Acetylation; D000480:Alkynes / Q000737:chemistry; D000440:Butanols / Q000737:chemistry*; D002853:Chromatography, Liquid / Q000379:methods; D007202:Indicators and Reagents; D008049:Lipase / Q000378:metabolism / Q000494:pharmacology*; D008698:Mesylates / Q000737:chemistry*; D008722:Methods; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
C448622:4-trimethylsilyl-3-butyn-2-ol; D000480:Alkynes; D000440:Butanols; D007202:Indicators and Reagents; D008698:Mesylates; D020005:Propanols; D014297:Trimethylsilyl Compounds; C028255:propargyl alcohol; D008049:Lipase