Diastereoselective synthesis of syn-1,3-diols by titanium-mediated reductive coupling of propargylic alcohols.
A titanium-mediated, hydroxy-directed reductive coupling reaction of propargylic alcohols and aldehydes/ketones is described. Excellent diastereoselectivity and synthetically useful yields have been obtained for a range of substrates. This transformation has enabled a highly convergent three-component approach to syn-1,3-diols using (trimethylsilyl)acetylene as a C1 linchpin.
Tian
Guo-Qiang
GQ
Depeartment of Chemistry, Texas A&M University, College Station, Texas 77842-3092, USA.
Kaiser
Thomas
T
Yang
Jiong
J
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D000438:Alcohols; D009942:Organometallic Compounds; D014025:Titanium