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. 2005 Dec 7;127(48):16778-9.
doi: 10.1021/ja054085l.

Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: highly regioselective synthesis of cross-conjugated dienones

Reema K Thalji  1 , William R Roush
Affiliations

Remarkable phosphine-effect on the intramolecular aldol reactions of unsaturated 1,5-diketones: highly regioselective synthesis of cross-conjugated dienones

Reema K Thalji et al. J Am Chem Soc. .

Abstract

We report a phosphine-mediated intramolecular aldol cyclization of unsaturated diketones that proceeds with extremely high levels of regioselectivity for the cross-conjugated bicyclic dienone products. The sense of regioselectivity observed in this reaction is complementary to that obtained using traditional aldol conditions. Experimental evidence that supports the involvement of a phosphine Michael adduct is described.

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Figures

Scheme 1
Scheme 1
Synthesis of Cross-Conjugated or Linear Dienones
See this image and copyright information in PMC

References

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