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Issue 12, 2011
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Asymmetric synthesis of highly functionalized cyclopentanes by a rhodium- and scandium-catalyzed five-step domino sequence

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Abstract

A domino sequence has been developed between vinyldiazoacetates and racemic allyl alcohols, involving five distinct steps. The sequence generates highly functionalized cyclopentanes with four new stereogenic centers as single diastereomers in 64–92% ee. The first step is a rhodium-catalyzed oxygen ylide formation, which is then followed by a [2,3]-sigmatropic rearrangement, an oxy-Cope rearrangement, a keto/enol tautomerization, and then finally a carbonyl ene reaction. With appropriate substrates, a further silyl deprotection and a 6-exo-trigcyclization can be added to the domino process.

Graphical abstract: Asymmetric synthesis of highly functionalized cyclopentanes by a rhodium- and scandium-catalyzed five-step domino sequence

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Article information


Submitted
07 Jul 2011
Accepted
04 Aug 2011
First published
02 Sep 2011

Chem. Sci., 2011,2, 2378-2382
Article type
Edge Article

Asymmetric synthesis of highly functionalized cyclopentanes by a rhodium- and scandium-catalyzed five-step domino sequence

B. T. Parr, Z. Li and H. M. L. Davies, Chem. Sci., 2011, 2, 2378
DOI: 10.1039/C1SC00434D

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