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Synthesis 2007(18): 2809-2818
DOI: 10.1055/s-2007-983884
DOI: 10.1055/s-2007-983884
PAPER
© Georg Thieme Verlag Stuttgart · New York
Iterative Synthesis of Oligo-1,4-diols via Catalytic Anti-Markovnikov Hydration of Terminal Alkynes
Further Information
Received
24 January 2007
Publication Date:
29 August 2007 (online)
Publication History
Publication Date:
29 August 2007 (online)
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Abstract
A sequential, iterative synthesis of oligo-1,4-diol building blocks has been realized via (a) propargylation of an aldehyde with allenylzinc bromide, (b) alcohol protection and (c) ruthenium-catalyzed anti-Markovnikov hydration of the terminal alkyne to release an aldehyde for the next iteration. Linear chains with 1,4-, 1,4,7- 1,4,7,10- and 1,4,7,10,13- functionalization patterns have been obtained by consecutive sequential iterations.
Key words
addition reactions - aldehydes - alkynes - homogeneous catalysis - ruthenium
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