19 research outputs found

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

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    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

    Efficient Access to Fused Ring Compounds via Dearomatization/Ring-Closing Metathesis

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    The complex (p-methoxyphenyl oxazoline)Cr(CO)3 is converted in two steps into a cis-fused [6,8] ring system containing a cycohexadiene ring unit, a cyclooctenone ring and a quaternary carbon at the ring junction. The key steps involve a diastereoselective addition of three C-substituents across an arene double bond, followed by an allylation and ring closing metathesis step. cis-Fused [6,7], [6,6], and [6,5] ring systems are also accessible via this methodology
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