Issue 19, 2014

Enantioselective construction of vicinal all-carbon quaternary centers via catalytic double asymmetric decarboxylative allylation

Abstract

We report a catalytic stereoconvergent construction of vicinal all-carbon quaternary centers via double stereoablative enantioselective alkylation of a mixture having racemic and meso diastereomers of esters to afford exceptional levels of diastereo- (up to 17 : 1) and enantioselectivity (up to >99% ee). The strategy offers an efficient and general approach to dimeric cyclotryptamine alkaloids sharing a labile C3a–C3a′ σ-bond in the hexahydropyrroloindoline core.

Graphical abstract: Enantioselective construction of vicinal all-carbon quaternary centers via catalytic double asymmetric decarboxylative allylation

Supplementary files

Article information

Article type
Communication
Submitted
27 Nov 2013
Accepted
19 Dec 2013
First published
23 Dec 2013

Chem. Commun., 2014,50, 2434-2437

Enantioselective construction of vicinal all-carbon quaternary centers via catalytic double asymmetric decarboxylative allylation

S. Ghosh, S. Bhunia, B. N. Kakde, S. De and A. Bisai, Chem. Commun., 2014, 50, 2434 DOI: 10.1039/C3CC49064E

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