Amphiphilic Allylic Alkylation with Allyl Alcohols Promoted by Pd-Catalyst and Triethylborane

Masanari      Kimura; Yoshinao      Tamaru

doi:10.2174/157019309789371631

Abstract

The combination of Pd catalyst and triethylborane induces allylic alcohols to undergo direct electrophilic allylation of soft nucleophiles. Similar conditions also accelerate nucleophilic allylations of aldehydes and aldimines to provide homoallyl alcohols and homoallylamines, respectively. Moreover, 2-methylenepropane-1,3-diol undergoes a sequential amphiphilic activation to react with aldehydes and aldimines, giving rise to 3-methylenecyclopentanols and 3-methylenepyrrolidines.

Keywords: Palladium, amphiphilic allylation, allyl alcohol, triethylborane, pyrrolidine

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Mini-Reviews in Organic Chemistry

Title: Amphiphilic Allylic Alkylation with Allyl Alcohols Promoted by Pd-Catalyst and Triethylborane

Volume: 6 Issue: 4

Author(s): Masanari Kimura and Yoshinao Tamaru

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Keywords: Palladium, amphiphilic allylation, allyl alcohol, triethylborane, pyrrolidine

Abstract: The combination of Pd catalyst and triethylborane induces allylic alcohols to undergo direct electrophilic allylation of soft nucleophiles. Similar conditions also accelerate nucleophilic allylations of aldehydes and aldimines to provide homoallyl alcohols and homoallylamines, respectively. Moreover, 2-methylenepropane-1,3-diol undergoes a sequential amphiphilic activation to react with aldehydes and aldimines, giving rise to 3-methylenecyclopentanols and 3-methylenepyrrolidines.

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Kimura Masanari and Tamaru Yoshinao, Amphiphilic Allylic Alkylation with Allyl Alcohols Promoted by Pd-Catalyst and Triethylborane, Mini-Reviews in Organic Chemistry 2009; 6 (4) . https://dx.doi.org/10.2174/157019309789371631