Issue 36, 2011
From the journal:

Chemical Communications

Catalytic enantioselective Grignard Nozaki–Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability‡†

Abbas Hassan,a   Ian A. Townsenda  and  Michael J. Krische*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, USA
E-mail: mkrische@mail.utexas.edu
Fax: +1 613 9418447
Tel: +1 512 2325892

Abstract

Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki–Hiyama methallylations from the alcohol or aldehyde oxidation level viairidium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetate does not react efficiently. Double methallylation of 1,3-propanediol provides the C2-symmetric adduct as a single enantiomer, as determined by HPLC analysis.

Graphical abstract: Catalytic enantioselective Grignard Nozaki–Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability

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Article information

DOI
https://doi.org/10.1039/C1CC14392A
Article type
Communication
Submitted
20 Jul 2011
Accepted
20 Jul 2011
First published
10 Aug 2011

Chem. Commun., 2011,47, 10028-10030

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Catalytic enantioselective Grignard Nozaki–Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability

A. Hassan, I. A. Townsend and M. J. Krische, Chem. Commun., 2011, 47, 10028 DOI: 10.1039/C1CC14392A

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