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. 2016 Feb 11:12:253-9.
doi: 10.3762/bjoc.12.27. eCollection 2016.

A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates

Hong-Bo Zhang  1 , Yong-Chun Luo  1 , Xiu-Qin Hu  1 , Yong-Min Liang  1 , Peng-Fei Xu  1
Affiliations

A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates

Hong-Bo Zhang et al. Beilstein J Org Chem. .

Abstract

A new and efficient synthetic method to obtain fully-substituted hexahydroisoindolinones was developed by using bifunctional tertiary amine-thioureas as powerful catalysts. As far as we know, there is no efficient synthetic method developed toward fully-substituted hexahydroisoindolinones. The products were obtained in good yield and diastereoselectivity. The one-pot cascade quadruple protocol features readily available starting materials, simple manipulation, mild conditions and good atom economy.

Keywords: bifunctional catalysis; hexahydroisoindolinones; one-pot synthesis; quadruple cascade.

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Figures

Scheme 1
Scheme 1
An example of scalable synthesis.
Scheme 2
Scheme 2
Hydrolysis reaction to produce a useful product.
Scheme 3
Scheme 3
Proposed mechanism.
See this image and copyright information in PMC

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