On the Origin of E/Z Selectivity in the Modified Julia Olefination - Importance of the Elimination Step
(2013) European Journal of Organic Chemistry — Vol. 2013, n° 5, p. 836-840 (2013)
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- Abstract
- The mechanism and origin of high E selectivity in the modified Julia olefination of aromatic aldehydes have been explored by computational and experimental means. Reversibility of addition and hence selectivity of the formation of sulfinate 5 is very variable and depends on the nature of the sulfone substrate. However, in all cases, elimination occurs through a concerted antiperiplanar and synperiplanar mechanism for sulfinates anti-5 and syn-5, respectively. Both syn and anti diastereomeric pathways thus lead preferentially to the (E)-alkene. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Robiette, R., & Pospíšil, J. (2013). On the Origin of E/Z Selectivity in the Modified Julia Olefination - Importance of the Elimination Step. European Journal of Organic Chemistry, 2013(5), 836-840. https://doi.org/10.1002/ejoc.201201634 (Original work published 2013)