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Synfacts 2019; 15(08): 0890
DOI: 10.1055/s-0039-1689804
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

The Catalytic Kulinkovich Reaction

Contributor(s):
Mark Lautens
,
Egor M. Larin
Kulinkovich OG. * Sviridov SV, Vasilevski DA. Belorussian State University, Minsk, USSR
Titanium(IV) Isopropoxide-Catalyzed Formation of 1-Substituted Cyclopropanols in the Reaction of Ethylmagnesium Bromide with Methyl Alkanecarboxylates.

Synthesis 1991; 234
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Publication History

Publication Date:
18 July 2019 (online)

 
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Key words

cyclopropanols - titanium catalysis - Kulinkovich reaction

Significance

The Kulinkovich reaction generates cyclopropanols from simple Grignard reagents and esters in the presence of a titanium(IV) alkoxide catalyst. This reaction has been subsequently expanded to a wide range of substrates (see Review below) and an asymmetric version was also demonstrated by the group of Corey (J. Am. Chem. Soc. 1994, 116, 9345).


 

Review

O. G. Kulinkovich, A. de Meijere Chem. Rev. 2000, 100, 2789–2834.


 

Comment

Although the group of Kulinkovich previously reported the synthesis of cyclopropanols through a titanium(IV) alkoxide mediated reaction (Zh. Org. Khim. 1989, 25, 2244), the current report demonstrated a method that was catalytic in titanium.


 

 


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