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

Marshall, James A.; Chobanian, Harry R.; Yanik, Mathew M.

doi:10.1021/ol016605x.s002

ol016605x_si_002.pdf (60.8 kB)

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

journal contribution

posted on 2001-09-25, 00:00 authored by James A. Marshall, Harry R. Chobanian, Mathew M. Yanik

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.