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Synlett 1991; 1991(11): 819-820
DOI: 10.1055/s-1991-20889
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A Chiral Acyclic Bis-allylic Compound as a Dienophile for Asymmetric Diels-Alder Reactions

Seiki Saito* , Hiroshi Hama, Yoshimasa Matsuura, Keiji Okada, Toshio Moriwake
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushima, Okayama 700, Japan
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Publication Date:
07 March 2002 (online)

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A chiral bis-allylic compound, diethyl (4S,5S)-4, 5-bis(tert-butyldimethylsilyloxy)-2,6-octadienedioate, has been used as a chiral dienophile to give [4+2] cycloadducts with several dienes in very high diastereomeric excess (>99%). One of the cycloadducts prepared from cyclopentadiene has led to aminobicyclo[2.2.1]heptane derivatives which are closely related to the TXA2 antagonist family.