Dual platinum and pyrrolidine catalysis in the direct alkylation of allylic alcohols: Selective synthesis of monoallylation products

Ryozo Shibuya, Lu Lin, Yasuhito Nakahara, Kazushi Mashima, Takashi Ohshima

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity. Two cats are better than one: The combined use of platinum and pyrrolidine catalysts enabled the direct alkylation of allylic alcohols with reactive methylene compounds. Pyrrolidine was essential for obtaining high selectivity of the monoallylation products, which were produced without the use of excess nucleophiles. cod=1,5- cyclooctadiene, EWG=electron-withdrawing group.

Original languageEnglish
Pages (from-to)4377-4381
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number17
DOIs
Publication statusPublished - Apr 22 2014

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Alkylation
Platinum
Catalysis
Alcohols
Nucleophiles
Acetic acid
Catalysts
Electrons
Acetic Acid
pyrrolidine
allyl alcohol

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Dual platinum and pyrrolidine catalysis in the direct alkylation of allylic alcohols : Selective synthesis of monoallylation products. / Shibuya, Ryozo; Lin, Lu; Nakahara, Yasuhito; Mashima, Kazushi; Ohshima, Takashi.

In: Angewandte Chemie - International Edition, Vol. 53, No. 17, 22.04.2014, p. 4377-4381.

Research output: Contribution to journalArticle

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