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Paper | Special issue | Vol 50, No. 2, 1999, pp.703-711
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)60
First Synthesis and Crystal Structures of Chiral 1,3-Dienylborates

Jacques Mortier,* Michel Vaultier, Barbara Plunian, and Loïc Toupet

*Université Rennes-I, Synthèse et èlectrosynthesse organiques, UMR 6510 Associée au CNRS, Campus de Beaulieu, 35042 Rennes Cedex, France


We repot on the synthesis of bicyclic 1,3-dienylborates (1a/1b and 2a/2b), wherein the boron and nitrogen atoms are chiral. The absolute configuration of these molecules was established by single X-Ray diffraction studies and qualitative homonuclear NOE difference spectroscopy. The conformational stability of these molecules is low at ambient or subambient temperature. The diastereomeric borates (2a/2b) were found to be very reactive toward dienophiles in the Diels-Alder reaction.