Issue 72, 2018
From the journal:

RSC Advances

Enantioselective Nozaki–Hiyama–Kishi allylation-lactonization for the syntheses of 3-substituted phthalides†

Sharad V. Kumbhara  and  Chinpiao Chen*ab  

* Corresponding authors

a Department of Chemistry, National Dong Hwa University, Shoufeng, Hualien 974, Taiwan
E-mail: chinpiao@gms.ndhu.edu.tw
Fax: +886 3 863 0475
Tel: +886 3 863 3597

b Department of Nursing, Tzu Chi University of Science and Technology, Hualien 970, Taiwan

Abstract

We report the synthesis of bipyridyl ligands and these ligands were applied in the chromium-catalyzed enantioselective Nozaki–Hiyama–Kishi allylation of substituted (2-ethoxycarbonyl)benzaldehydes and subsequently lactonized to synthesize phthalides with an optimal enantioselectivity of 99%. This approach was applied to synthesize (S)-cytosporone E at a 71% yield in three steps.

Graphical abstract: Enantioselective Nozaki–Hiyama–Kishi allylation-lactonization for the syntheses of 3-substituted phthalides

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Article information

DOI
https://doi.org/10.1039/C8RA09575B
Article type
Paper
Submitted
21 Nov 2018
Accepted
23 Nov 2018
First published
12 Dec 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 41355-41357

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Enantioselective Nozaki–Hiyama–Kishi allylation-lactonization for the syntheses of 3-substituted phthalides

S. V. Kumbhar and C. Chen, RSC Adv., 2018, 8, 41355 DOI: 10.1039/C8RA09575B

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