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Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes

✍ Scribed by Ryuji Matsumura; Toshio Suzuki; Kohki Sato; Takashi Inotsume; Hisahiro Hagiwara; Takashi Hoshi; Vijayendra P Kamat; Masayoshi Ando

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
86 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

An efficient and versatile method for the stereospecific construction of a,v-cisand a,v-trans-disubstituted oxepane skeletons is described. Cyclization of the hydroxy epoxides promoted by a (Bu 3 Sn) 2 O/ Zn(OTf) 2 system proceeded via an S N 2 process and exo mode selectivity regardless of the configuration of the hydroxyl and the epoxy groups to provide the corresponding oxepanes in excellent yields.

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