Catalytic Asymmetric and Stereoselective Synthesis of Vinylcyclopropanes

Swapan Majumdar; Armin de Meijere; Ilan Marek

doi:10.1055/s-2002-20456

LETTER

Catalytic Asymmetric and Stereoselective Synthesis of Vinylcyclopropanes

Swapan Majumdar^a, Armin de Meijere^b, Ilan Marek*^a
^a Department of Chemistry and Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Technion City, 32000 Haifa, Israel
Fax: +972(4)82937 09; e-Mail: chilanm@tx.technion.ac.il;
^b Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077 Göttingen, Germany

Abstract

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Abstract

The first sequential catalytic asymmetric carbolithiation reaction of dienyl systems followed by a 1,3-intramolecular elimination leads to (E)- and trans-disubstituted vinylcyclopropanes in moderate to good enantiomeric excesses.

Key words

carbometallation - (-)-sparteine - chirality - vinylcyclopropanes - asymmetric catalysis

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References

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Specific rotations for vinylcyclopropane derivatives: 12a [α]_D ²⁵ = -13.33 (c 0.60, CHCl₃); 12b [α]_D ²⁵ = -11.66 (c 1.2, CHCl₃); 13a [α]_D ²⁵ = -46.6 (c 1.67, CHCl₃); 13b [α]_D ²⁵ = -23.3 (c 1.2, CHCl₃); 14a [α]_D ²⁵ = -25.45 (c 1.12, CHCl₃); 14b [α]_D ²⁵ = -17.5 (c 0.80, CHCl₃); 15a [α]_D ²⁵ = -8.24 (c 1.7, CHCl₃); 15b [α]_D ²⁵ = -7.69 (c 1.04, CHCl₃); 17 [α]_D ²⁵ = -20.0 (c 0.80, CHCl₃).