Synfacts 2017; 13(10): 1041
DOI: 10.1055/s-0036-1591250
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Synthesis of Alkylidenecyclobutanes

Contributor(s): Mark Lautens, Ivan Franzoni
Eisold M. Didier D. * Ludwig-Maximilians-Universität München, Germany
Stereoselective Access to Alkylidenecyclobutanes through γ-Selective Cross-Coupling Strategies.

Org. Lett. 2017;
19: 4046-4049
Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
Zoom Image

Significance

Alkylidenecyclobutanes are useful strained building blocks that can also be found in a number of natural compounds. In this work, the authors disclose the use of a γ-selective Suzuki–Miyaura cross-coupling for the synthesis of this class of compounds containing a quaternary stereocenter.


#

Comment

Achiral cyclobutenylmethylboronic esters reacted with aryl halides in the presence of a palladium catalyst and potassium hydroxide. The corresponding products were obtained in moderate to excellent yields and essentially with perfect γ-selectivity. In the case of δ-substituted substrates, high levels of diastereoselectivity were ­obtained. The use of (chiral) α-substituted starting materials generated the corresponding products containing a trisubstituted double bond functionality in high stereoselectivity (and enantioselectivity).


#
#


Zoom Image