STEREOCONTROL IN DIELS-ALDER CYCLOADDITION TO UNSATURATED SUGARS - REACTIVITIES OF ACYCLIC 7-CARBON TRANS DIENOPHILES DERIVED FROM ALDOPENTOSES

被引:7
作者
HORTON, D [1 ]
KOH, D [1 ]
机构
[1] OHIO STATE UNIV, DEPT CHEM, COLUMBUS, OH 43210 USA
关键词
D O I
10.1016/0008-6215(93)84004-P
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Acyclic trans-2,3-unsaturated aldoheptonate derivatives (1-9) obtained from D-aldopentoses by Wittig chain-extension served as dienophiles for a detailed comparative study of their asymmetric Diels-Alder cycloaddition with cyclopentadiene. Cycloaddition under uncatalyzed thermal conditions gave mixtures of the four possible stereoisomeric norbornene adducts. The endo:exo ratios and the diastereofacial selectivities in the formation of the adducts were determined by NMR spectroscopy and by chemical transformations. The quantitative distribution of adducts as a function of stereochemistry of the dienophile is discussed.
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收藏
页码:249 / 260
页数:12
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