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Synfacts 2006(8): 0809-0809
DOI: 10.1055/s-2006-942016
DOI: 10.1055/s-2006-942016
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric [5+2] Cycloaddition of Vinylcyclopropanes and π-Systems
P. A. Wender*, L. O. Haustedt, J. Lim, J. A. Love, T. J. Williams, J.-Y. Yoon
Stanford University, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Juli 2006 (online)
Significance
Wender’s group has extended its [5+2] cycloaddition-reaction arsenal. They found that Rh(I)/BINAP is a superior catalyst for the cycloaddition of vinylcyclopropanes tethered to alkenes for the intramolecular variant. The substrates containing synthetically useful sulfonamide and malonodiester groups gave high yields and excellent enantioselectivities. Substitution at the cyclopropane group as well as internal substitution on the terminal alkene resulted in high selectivity. Alkyne-substituted substrates showed low ee values, as did a substrate with an internal hydrogen on the terminal alkene when the malonodiester was present in the tether.