A Formal [4+4] Complementary Ambiphile Pairing Reaction: A New Cyclization Pathway for ortho-Quinone Methides

被引：55
作者：
Samarakoon, Thiwanka B.
Hur, Moon Y.
Kurtz, Ryan D.
Hanson, Paul R. [1 ]
机构：
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 10期
基金：
美国国家科学基金会;
关键词：
COMPLEXES; STRATEGY;
D O I：
10.1021/ol100495w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.
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收藏
页码：2182 / 2185
页数：4
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