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Title

Synthesis of [6,n] cis-fused ring compounds via Cr-mediated dearomatisation-ring-closing metathesis

Authors
Bellido, Alejandro
Published in Organic and Biomolecular Chemistry. 2006, vol. 4, no. 2, p. 342-351
Abstract cis-Fused [6,8], [6,7], [6,6] and [6,5] ring systems containing a cyclohexadiene ring unit, a cycloenone ring and a quaternary carbon at the ring junction were obtained in only two steps from [Cr(CO)3(eta6-p-methoxyphenyl oxazoline)]. The sequence proceeds via diastereoselective addition of three C-substituents across an arene double bond, followed by allylation and ring closing metathesis (RCM). RAMP-hydrazone and (R)-isopropyloxazoline were used as chiral auxiliaries to provide, after removal of the auxiliaries, the enantiomerically highly enriched [6,7] cis-fused system.
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PMID: 16391777
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KUNDIG, Ernst Peter et al. Synthesis of [6,n] cis-fused ring compounds via Cr-mediated dearomatisation-ring-closing metathesis. In: Organic and Biomolecular Chemistry, 2006, vol. 4, n° 2, p. 342-351. https://archive-ouverte.unige.ch/unige:6927

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Deposited on : 2010-06-18

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