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Synfacts 2014; 10(8): 0849
DOI: 10.1055/s-0034-1378489
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of syn-Homoallylic Alcohols

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Miura T, * Nishida Y, Murakami M. * Kyoto University, Japan
Construction of Homoallylic Alcohols from Terminal Alkynes and Aldehydes with Installation of syn-Stereochemistry.

J. Am. Chem. Soc. 2014;
136: 6223-6226
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Further Information

Publication History

Publication Date:
18 July 2014 (online)

 
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Key words

silaboration - rhodium - syn-homoallylic alcohols

Significance

The authors established a new synthetic method for the synthesis of syn-homoallylic alcohols from terminal alkynes and aldehydes. As this transformation utilizes easily accessible starting materials, this practical method should find many applications.


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Comment

A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronates, which can be easily prepared from a terminal alkyne, into the corresponding allylboronate, that directly undergoes nucleophilic addition to an aldehyde to afford the corresponding syn-homoallylic alcohol in excellent stereoselectivity.


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