From Catalysis to Lewis Base Catalysis with Highlights from 1806 to 1970

Vedejs, E.

doi:10.1002/9783527675142.ch1

Cited by 11 publications

(15 citation statements)

References 112 publications

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“…As part of an ongoing program on the enantioselective functionalization of alkenes, we have exploited the activation of group 16 Lewis acids by Lewis bases to access seleno- and sulfenofunctionalized products. 7 Association of a Lewis basic selenophosphoramide catalyst 5 and group 16 Lewis acid 4 (“Sulfenylating Agent”) results in a highly electrophilic donor–acceptor complex. 8 This complex is intercepted by an unactivated alkene to form an enantioenriched, configurationally stable thiiranium ion which subsequently undergoes stereospecific nucleophilic opening.…”

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confidence: 99%

Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes

Roth

Denmark

2019

J. Am. Chem. Soc.

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A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.

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confidence: 99%

Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes

Roth

Denmark

2019

J. Am. Chem. Soc.

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“…13 In group 16, activation of S -arylthioph-thalimides with chiral Lewis basic catalysts allows for the formation of enantiomerically enriched thiiranium ions from unactivated alkenes. 14a,b These thiiranium ions may be intercepted by pendant nucleophiles to form a wide variety of 1,2-sulfeno-functionalized products in a highly stereoselective fashion.…”

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confidence: 99%

Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

et al. 2018

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A sulfenium-ion-initiated, catalytic, enantio-selective polyene cyclization is described. Homogeranylar-enes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantio-merically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.

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“…1–5 For many applications which revolve around electron donation in the liquid phase, e.g. electrochemical energy storage and catalysis, 6–10 knowledge of the occupied electronic states is vital for understanding and predicting reactivity. Experimental measures of the occupied valence states (OVSs) 11 and calculations of the occupied molecular orbitals (OMOs) 1–5,12 for gas phase molecules and for solids/adsorbates on solids are widely available.…”

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confidence: 99%