Dual Platinum and Pyrrolidine Catalysis in the Direct Alkylation of Allylic Alcohols: Selective Synthesis of Monoallylation Products

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 reac...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-04, Vol.53 (17), p.4377-4381
Main Authors: Shibuya, Ryozo, Lin, Lu, Nakahara, Yasuhito, Mashima, Kazushi, Ohshima, Takashi
Format: Article
Language:English
Subjects:
Acetic acid
Alcohols
Alkylation
Allyl Compounds - chemical synthesis
allylic alkylation
Catalysis
Cats
homogeneous catalysis
Methylene
Molecular Structure
Nucleophiles
organocatalysis
Platinum
Platinum - chemistry
Propanols - chemistry
pyrrolidine
Pyrrolidines - chemistry
Selectivity
Stereoisomerism
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201311200