Stereoselectivity control by torsional steering in an intramolecular Diels-Alder reaction of vinyl oxocarbenium ions
Stereoselectivity control by torsional steering in an intramolecular Diels-Alder reaction of vinyl oxocarbenium ions
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DOI：
10.1021/ol061085x
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发表时间：
2006-08-03
期刊：
影响因子：
5.2
通讯作者：
Houk, K. N.
中科院分区：
文献类型：
--
作者：
Iafe, Robert G.;Houk, K. N.
Density functional theory (B3LYP/6-31+ G*) has revealed the origin of stereoselectivity in intramolecular Diels- Alder reactions of vinyl oxocarbenium ions. The cycloaddition has endo preference and occurs with remote stereocontrol syn to the substituent at the stereogenic center. Torsional steering, the preference for the staggered conformation about forming sigma-bonds, dictates the preferred transition structure.
