2017
DOI: 10.1002/ejoc.201701280
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Chiral Inductive Diastereoconvergent Friedel–Crafts Alkylation Reaction of Diastereomixtures of Diarylmethanols with 2‐Naphthol Derivatives Catalyzed by SnBr4

Abstract: A highly diastereoconvergent Friedel–Crafts alkylation reaction of 2‐naphthol derivatives with diastereomixtures of diarymethanols bearing a designed chiral auxiliary was achieved by using tin(IV) bromide as a catalyst in nitromethane under mild reaction conditions. The effects of various substituents located on the chiral auxiliary were evaluated, and chiral induction was found to take place via a carbocation through the chelation effect of an oxygen atom in a stereoconvergent manner. The chiral auxiliary was… Show more

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Cited by 18 publications
(39 citation statements)
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“…As a result, although the rate of the reaction involving ( R , S )‐ 8a was higher than that of ( S , S )‐ 8a , the same diastereomeric mixture of ( R , S )‐ 10a was obtained with almost equally high diastereoselectivity, irrespective of the stereochemistry of the starting material. These results suggest that the reaction proceeds via the dibenzyl cation in a chiral‐inductive diastereoconvergent manner, as previously revealed by our group …”
Section: Resultssupporting
confidence: 85%
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“…As a result, although the rate of the reaction involving ( R , S )‐ 8a was higher than that of ( S , S )‐ 8a , the same diastereomeric mixture of ( R , S )‐ 10a was obtained with almost equally high diastereoselectivity, irrespective of the stereochemistry of the starting material. These results suggest that the reaction proceeds via the dibenzyl cation in a chiral‐inductive diastereoconvergent manner, as previously revealed by our group …”
Section: Resultssupporting
confidence: 85%
“…In order to optimize the reaction conditions, as a model reaction, we chose to react a diastereomeric mixture of diarylmethanol 8a (diastereomeric ratio dr = ca. 60:40) with allyltrimethylsilane and examined the effect of the solvent, reaction temperature, and Lewis acid (Table ). We first performed the reaction in MeNO 2 at room temperature in the presence of 5 mol‐% of SnBr 4 as the catalyst, following previously reported conditions .…”
Section: Resultsmentioning
confidence: 99%
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