Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes

被引：37

作者：

Crowley, PJ

Fawcett, J

Kariuki, BM

Moralee, AC

Percy, JM ^{[1
]}

Salafia, V

机构：

[1] Syngenta Ltd, Jealotts Hill Int Res Ctr, Bracknell RG42 6ET, Berks, England

[2] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

[3] Univ Birmingham, Sch Chem Sci, Birmingham B15 2TT, W Midlands, England

[4] Univ Birmingham, Sch Chem Sci, Birmingham B15 2TT, W Midlands, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 23期

关键词：

D O I：

10.1021/ol0268743

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC = CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.

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页码：4125 / 4128

页数：4

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