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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).


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Review

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


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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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