Studies into the stereoselectivity of tartrate-derived dienophiles.
[reaction: see text] Diels-Alder reactions of 1-(tert-butyldimethylsiloxy)-1,3-butadiene (3) with three C2 symmetric dienophiles derived from tartaric acid have been examined. Complementary diastereoselectivity is observed depending on the nature of the 1,2-diol protecting group incorporated in these dienophiles.
Lee
Wei-Der
WD
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Kim
Kwangho
K
Sulikowski
Gary A
GA
D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
C507451:1-(tert-butyldimethylsiloxy)-1,3-butadiene; D002070:Butadienes; D013644:Tartrates; C029768:tartaric acid