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Letter

Cross-Coupling for Cross-Conjugation: Practical Synthesis and Diels−Alder Reactions of [3]Dendralenes

Supporting Info

Tanya A. Bradford,^† Alan D. Payne,^† Anthony C. Willis,^†^‡ Michael N. Paddon-Row,*^§ and Michael S. Sherburn*^†^¶;

Research School of Chemistry, The Australian National University, Canberra ACT 0200, Australia, and School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia

Org. Lett., 2007, 9 (23), pp 4861–4864

DOI: 10.1021/ol7021998

Publication Date (Web): October 11, 2007

†

The Australian National University.

‡

To whom correspondence should be addressed regarding X-ray crystal structures. E-mail: willis@rsc.anu.edu.au.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

The University of New South Wales.

ARC Centre of Excellence for Free Radical Chemistry and Biotechnology.

, sherburn@rsc.anu.edu.au (synthetic), ; , m.paddonrow@unsw.edu.au (computational)

Abstract

The parent [3]dendralene and 2-substituted [3]dendralenes are made easily through cross-coupling reactions. Contrary to some earlier reports, [3]dendralene is sufficiently stable to be handled using standard synthetic methods. These compounds allow the one-step stereoselective construction of polycyclic frameworks through reactions with dienophiles. Site selectivity and stereoselectivity in Diels−Alder reactions with dienophiles are generally not influenced by the nature of the [3]dendralene's 2-substituent; these features can, however, be influenced with Lewis acids.

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