Synthesis of functionalized cis-fused bicarbocyclic structures via olefin cross metathesis and tandem conjugate/Michael addition

Posted May 14th, 2010 at 2:34 pm.

Yuan Qiao
Mentor: Dr. W. Malachowski

Syntheses of cis-fused bicarbocyclic systems are of great interest for constructing complex organic architectures. We report a new synthetic method to functionalized bicarbocyclic structures using the final product from the Birch-Cope sequence that has been developed by the Malachowski group. The two-step method (Scheme 1) includes an olefin cross metathesis and a tandem conjugate/Michael addition.

qiao1

A wide range of olefin cross metathesis alkenes and a variety of conjugate addition nucleophiles are explored to illustrate the versatility of this synthetic strategy. The alkenes (Table 1) chosen are commercially available and all have precedent for their use in olefin metathesis. It has been shown that 2.5mol% of second generation Hoveyda-Grubb’s catalyst afforded excellent yields with the listed alkenes. The nucleophiles (Table 1) for tandem conjugate/Michael addition come in several forms: non-stabilized carbon nucleophiles, stabilized carbon nucelophiles, heteroatom nucleophiles and carbon radicals. Our work demonstrates the accessibility of constructing functionalized cis-fused bicarbocyclic structures using this tool.

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Filed under: 2009,Malachowski, Dr. William,Qiao, Yuan by Ann Dixon

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