β-acyloxysulfonyl tethers for intramolecular Diels-Alder cycloaddition reactions

被引：16
|
作者：
Chumachenko, N [1 ]
Sampson, P
Hunter, AD
Zeller, M
机构：
[1] Kent State Univ, Dept Chem, Kent, OH 44242 USA
[2] Youngstown State Univ, Dept Chem, Youngstown, OH 44555 USA
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 15期
关键词：
D O I：
10.1021/ol050930t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
beta-Hydroxy sulfone-based tethers were employed for the first time to achieve thermally mediated intramolecular Diels-Alder cycloaddition. The reactions proceeded with complete regioselectivity and high (10/1) to complete endo/exo-selectivity and resulted in the preferential formation of one of the two possible endo-cycloadducts. The yields and stereoselectivities were proportional to the bulk of the R-1 substituent on the beta-acyloxysulfonyl tether.
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收藏
页码：3203 / 3206
页数：4
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