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Issue 29, 2018
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Catalytic asymmetric synthesis of geminal-dicarboxylates

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Abstract

Stereogenic acetals, spiroacetals and ketals are well-studied stereochemical features that bear two heteroatoms at a common carbon atom. These stereocenters are normally found in cyclic structures while linear (or acyclic) analogues bearing two heteroatoms are rare. Chiral geminal-dicarboxylates are illustrative, there is no current way to access this class of compounds while controlling the stereochemistry at the carbon center bound to two oxygen atoms. Here we report a rhodium-catalysed asymmetric carboxylation of ester-containing allylic bromides to form stereogenic carbon centers bearing two different carboxylates with high yields and enantioselectivities. The products, which are surprisingly stable to a variety of acidic and basic conditions, can be manipulated with no loss of enantiomeric purity as demonstrated by ring closing metathesis reactions to form chiral lactones, which have been extensively used as building blocks in asymmetric synthesis.

Graphical abstract: Catalytic asymmetric synthesis of geminal-dicarboxylates

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Article information


Submitted
19 Apr 2018
Accepted
28 Jun 2018
First published
28 Jun 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 6307-6312
Article type
Edge Article

Catalytic asymmetric synthesis of geminal-dicarboxylates

N. Mistry and S. P. Fletcher, Chem. Sci., 2018, 9, 6307
DOI: 10.1039/C8SC01786G

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