| Autor: |
Heafner, Elizabeth D., Lin, Xuechun, Connors, Alexa H., Zhong, Hanyu, Coyle, R. Joseph, Liu, Yiqi, Downey, C. Wade |
| Předmět: |
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| Zdroj: |
Synthesis; Aug2023, Vol. 55 Issue 15, p2377-2389, 13p |
| Abstrakt: |
Keywords: allylation; enol silane; one pot; alkylation; silyl triflates; Lewis acid catalysis; regioselectivity EN allylation enol silane one pot alkylation silyl triflates Lewis acid catalysis regioselectivity 2377 2389 13 07/14/23 20230801 NES 230801 Graph Allylation of ketones remains an active area of pursuit, with recent reports focusing upon the reaction of enol silanes, [1] enol acetates, [3] 1,3-dicarbonyls, [4] and simple unactivated ketones [6] with quasi-symmetrical allylic alcohols derived from chalcone. For example, a consistent color change from pale yellow to dark red or black was generally observed upon addition of TMSOTf to reaction mixtures containing allyl propionates, a change not observed when allyl propionate was absent; this color change may provide circumstantial evidence for the formation of the proposed carbocation. One-Pot Enol Silane Formation-Allylation of Ketones Promoted by Trimethylsilyl Trifluoromethanesulfonate While both allyl acetates and allyl propionates proved to be active carbocation precursors under the reaction conditions, allyl propionates provided consistently cleaner conversion to the desired product, and their use suppressed competing [3,3] and [1,3] rearrangements of the starting material. [Extracted from the article] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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