Stereoselectivities of benzonitrile oxide cycloadditions to disubstituted cyclopentenes and dihydrofurans
1984; Elsevier BV; Volume: 25; Issue: 18 Linguagem: Inglês
10.1016/s0040-4039(01)90064-4
ISSN1873-3581
AutoresPierluigi Caramella, Franca Marinone Albini, Dario Vitali, Nelson G. Rondan, Yun‐Dong Wu, Timothy R. Schwartz, K. N. Houk,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoBenzonitrile oxide cycloadds preferentially anti to the substituents of cis-3,5-di-X-cyclopentenes, where X = OMe, OAc, OCOPh, Br, Cl, and OH. Higher stereoselectivities are found for cis-2,5-di-X-2,5-dihydrofurans. The origins of these selectivities, and contrasts with acyclic and cyclobutene analogs, are described.
Referência(s)