Et2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy esters

D Yang, Q Gao, BF Zheng, NY Zhu

Index: Yang, Dan; Gao, Qiang; Zheng, Bao-Fu; Zhu, Nian-Yong Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8821 - 8828

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Citation Number: 21

Abstract

We have developed a new method for asymmetric phenylseleno group transfer radical cyclization of unsaturated β-hydroxy esters. Various unsaturated α-phenylseleno β-hydroxy esters underwent radical cyclization in the presence of Et2AlCl in benzene with sunlamp irradiation at 25-30° C to give mono-and bicyclic group-transferred products in an efficient and highly regioselective and diastereoselective manner. To rationalize the high ...