Chemical Communications

BF3· OEt2-mediated cycloaddition of O-tert-butyldimethylsilyloximes having olefin moieties: intramolecular cycloaddition of N-borano-nitrones

O Tamura, T Mitsuya, H Ishibashi

Index: Tamura, Osamu; Mitsuya, Takahiro; Ishibashi, Hiroyuki Chemical Communications, 2002 , # 10 p. 1128 - 1129

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Abstract

We initiated our investigation by the reaction of oxime 1a having a trans-cinnamyl moiety in the presence of Cu(OTf) 2 or BF 3 ĚOEt 2 (Table 1) taking into account their affinities to nitrogen. Treatment of oxime 1a (R = H) with Cu(OTf) 2 in acetonitrile at rt gave 3a in 16% yield (entry 1). When 1a (R = H) was treated with Cu(OTf) 2 in the presence of i-Pr 2 NEt, dehydration occurred to provide nitrile 4 (entry 2). This suggests that Cu(OTf) 2 may coordinate with the oxygen ...