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Synthesis 2013; 45(5): 592-595
DOI: 10.1055/s-0032-1317949
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A General Approach to Terminal Allenols

Jinqiang Kuang
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China
,
Xi Xie
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China
,
Shengming Ma*
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Linglin Lu, Shanghai 200032, P. R. of China   Fax: +86(21)62609305   Email: masm@sioc.ac.cn
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Publication History

Received: 11 October 2012

Accepted after revision: 03 December 2012

Publication Date:
24 January 2013 (online)

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Abstract

We have demonstrated a very general method for the preparation of essentially any terminal 2,3-allenol from the corresponding alkynols, which may be easily available from propargylic alcohols by alkylation, or from terminal alkynes by deprotonation and 1,2-addition with aldehydes or ketones, and subsequent base-catalyzed triple-bond migration.

Key words

copper(I) iodide - dicyclohexylamine - allenols - long carbon chain - chirality

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