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Issue 30, 2012
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Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system

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Abstract

The combined carbometalation–zinc homologation–allylation reaction of the resulting stereodefined 3,3-disubstituted allylmetal species with ketones allow the preparation of allylic vicinal diol derivatives in good yields with excellent diastereomeric ratios from commercially available alkynes. Two adjacent quaternary centers are formed with the concomitant formation of three new carbon–carbon bonds in a single-pot operation in an acyclic system. The bulky substituent of the ketone occupies a pseudo-axial position in the Zimmerman–Traxler transition state.

Graphical abstract: Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system

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Article information


Submitted
16 Jan 2012
Accepted
16 Feb 2012
First published
21 Feb 2012

Org. Biomol. Chem., 2012,10, 5803-5806
Article type
Communication

Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system

T. Mejuch, B. Dutta, M. Botoshansky and I. Marek, Org. Biomol. Chem., 2012, 10, 5803
DOI: 10.1039/C2OB25121C

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