Synfacts 2010(6): 0702-0702  
DOI: 10.1055/s-0029-1219774
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Transmetalation of (Z)-Telluroenynes: Stereoselective Synthesis of (Z)-Enynols

Contributor(s): Paul Knochel, Stefan Wunderlich
C. C. Schneider, H. Caldeira, B. M. Gay, D. F. Back, G. Zeni*
Universidade Federal de Santa Maria, Brazil
Further Information

Publication History

Publication Date:
20 May 2010 (online)

Significance

The synthesis of various (Z)-enynols is achieved via the reaction of alkenyl­lithium intermediates with aldehydes and ketones. These alkenyllithiums are obtained by a tellurium/lithium exchange. The subsequent cyclization of a broad variety of (Z)-enynols affords substituted furans and dihydrofurans with high regioselectivity under mild reaction conditions.