Highly diastereoselective synthesis of propargylic 1,2-anti-diol derivatives using alpha-alkoxypropargylstannanes.
Propargylic 1,2-anti-diol derivatives 2 and 10 are prepared in high yield and excellent diastereoselectivity by addition of alpha-alkoxypropargylstannanes 4a and 4b to aldehydes in the presence of BuSnCl(3). We also introduce the use of KF on Celite as a convenient and mild reagent for removal of the organotin waste products of these reactions. Reaction: see text.
Savall
B M
BM
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA.
Powell
N A
NA
Roush
W R
WR
D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis*; D001685:Biological Factors / Q000138:chemical synthesis; D020005:Propanols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry
D000447:Aldehydes; D000480:Alkynes; D001685:Biological Factors; D020005:Propanols; D017971:Tin Compounds; C031525:stannane; C028255:propargyl alcohol