ArticleJournal of the American Chemical Society2013
Origins of 1,6-stereoinduction in torquoselective 6π electrocyclizations.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines.Journal of the American Chemical Society · 2023Article
- Synthesis of ent-ketorfanol via a C-H alkenylation/torquoselective 6π electrocyclization cascade.Angewandte Chemie (International ed. in English) · 2015Article
- Functionalized α,α-dibromo esters through Claisen rearrangements of dibromoketene acetals.Organic letters · 2015Article
- Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products.Journal of the American Chemical Society · 2015Article
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Authors and funding
4 authors.
Funding
Abstract
A novel stereoselective electrocyclization developed for the total synthesis of reserpine has been explored by both experiment and theory. A stereocenter six atoms away from the newly forming chiral center is responsible for the diastereoselectivity of the ring closure. This stereogenic center, lying at the junction of two six-membered rings, defines the conformation of the substrates' fused ring skeleton that ultimately distinguishes between the two allowed, disrotatory triene geometries at the transition state. The presence of allylic strain in the disfavored transition state results in a torquoselective ring closure (dr up to 15.7:1).
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