Issue 30, 2012

Convergent diastereoselective preparation of adjacent quaternary stereocenters in an acyclic system

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

Supplementary files

Article information

Article type
Communication
Submitted
16 yan 2012
Accepted
16 fev 2012
First published
21 fev 2012

Org. Biomol. Chem., 2012,10, 5803-5806

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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