Palladium-catalyzed oxidations:: Inhibition of a Pd-H elimination by coordination of a remote carbon-carbon double bond

被引:12
作者
Aït-Mohand, S [1 ]
Hénin, F [1 ]
Muzart, J [1 ]
机构
[1] Univ Reims, CNRS, UMR React Select & Applicat, F-51687 Reims 2, France
关键词
D O I
10.1021/om001028m
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Under oxidative conditions that use an anionic palladium salt as catalyst, cis-endo-2,3-bis(hydroxymethyl)bicyclo[2.2.1]hept-5-ene affords the corresponding exo-lactol, while cis-endo-2,3-bis(hydroxymethyl)bicyclo[2.2.1]heptane provides the expected Lactone. Mechanistic considerations explain hero the presence of the C=C bond blocks the oxidation at the lactol in the first case.
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页码:1683 / 1686
页数:4
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