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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.
Publication status:
Published

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Publisher copy:
10.1021/ja410220w
Journal:
Journal of the American Chemical Society More from this journal
Volume:
136
Issue:
6
Pages:
2397-2403
Publication date:
2014-02-01
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Language:
English
Keywords:
Pubs id:
pubs:446829
UUID:
uuid:ca5f86f1-8b17-4c71-970f-6f626273fe5c
Local pid:
pubs:446829
Source identifiers:
446829
Deposit date:
2014-01-30

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