Studies on the regio- and stereoselectivity of halohydroxylation of 1,2-allenyl sulfides or selenides

Shengming Ma; Xueshi Hao; Xiaofeng Meng; Xian Huang

doi:10.1021/jo049593c

Studies on the regio- and stereoselectivity of halohydroxylation of 1,2-allenyl sulfides or selenides

J Org Chem. 2004 Aug 20;69(17):5720-4. doi: 10.1021/jo049593c.

Authors

Shengming Ma¹, Xueshi Hao, Xiaofeng Meng, Xian Huang

Affiliation

¹ Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China. masm@mail.sioc.ac.cn

PMID: 15307745
DOI: 10.1021/jo049593c

Abstract

It was observed that the halohydroxylation of 1,2-allenyl sulfides or selenides with Br2 (CuBr2 or NBS) or I2 and water demonstrated a fairly good regioselectivity (i.e., the C=C bond that is remote from the S or Se atom was halohydroxylated with the halogen atom connecting to the middle carbon atom and the hydroxyl group connecting to the non-S terminal carbon or Se-substituted terminal carbon atom of the allene moiety), leading to the synthesis of synthetically important 3-organosulfur or seleno-2-haloallylic alcohols. The stereoselectivity depends on the nature of X+ and S or Se, showing a Z-selectivity with the matched Lewis acid-base pair.