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Synlett 2010(14): 2169-2173  
DOI: 10.1055/s-0030-1258541
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

FeCl3-Promoted One-Step Synthesis of Spiro[4.5]decane Derivatives

Deping Zheng, Zuodong Ma, Wanchun Gong, Zhixiang Xie*, Ying Li*
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: xiezx@lzu.edu.cn; e-Mail: liying@lzu.edu.cn;
Further Information

Publication History

Received 22 March 2010
Publication Date:
30 July 2010 (online)

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Abstract

A FeCl3-promoted synthesis of spiro[4.5]decane derivatives has been developed from 2-(5,5-dimethoxypentyl)-1-substituted cyclopentanols with high diastereoselectivity. These interesting compounds are formed through a cascade process involving a FeCl3-promoted dehydration of alcohol followed by FeCl3-mediated Prins cyclization.

Key words

spiro[4.5]decane - FeCl3 - Prins cyclization - α-hydroxy alkynyl acetals - diastereoselectivity

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8

The preparation of 1a is described in the Supporting Information.

9

CCDC-781108 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/deposit [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax +44 (1223)336033; email: deposit@ccdc.cam.ac.uk].