Intramolecular Diels-Alder reactions of cycloalkenones: Stereoselectivity, lewis acid acceleration, and halogen substituent effects Journal Article
| Authors: | Pham, H. V.; Paton, R. S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. |
| Article Title: | Intramolecular Diels-Alder reactions of cycloalkenones: Stereoselectivity, lewis acid acceleration, and halogen substituent effects |
| Abstract: | The intramolecular Diels-Alder reactions of cycloalkenones and terminal dienes occur with high endo stereoselectivity, both thermally and under Lewis-acidic conditions. Through computations, we show that steric repulsion and tether conformation govern the selectivity of the reaction, and incorporation of either BF3 or α-halogenation increases the rate of cycloaddition. With a longer tether, isomerization from a terminal diene to the more stable internal diene results in a more facile cycloaddition. © 2014 American Chemical Society. |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 136 |
| Issue: | 6 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2014-02-12 |
| Start Page: | 2397 |
| End Page: | 2403 |
| Language: | English |
| DOI: | 10.1021/ja410220w |
| PROVIDER: | scopus |
| PMCID: | PMC3965351 |
| PUBMED: | 24410341 |
| DOI/URL: | |
| Notes: | Export Date: 3 March 2014 -- CODEN: JACSA -- Source: Scopus |
