Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones

Ruben P. van Summeren; Sven J. W. Reijmer; Ben L. Feringa; Adriaan J. Minnaard

doi:10.1039/B419268K

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Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones†

Ruben P. van Summeren,^a Sven J. W. Reijmer,^a Ben L. Feringa*^a and Adriaan J. Minnaard*^a

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* Corresponding authors

^a Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
E-mail: B.L.Feringa@chem.rug.nl., A.J.Minnaard@chem.rug.nl

Abstract

The first catalytic asymmetric procedure capable of preparing all 4 diastereoisomers (ee > 99%, de > 98%) of a versatile saturated isoprenoid building block was developed and the value of this new method was demonstrated in its application to the concise total synthesis of two pheromones.

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Supplementary files

Detailed experimental procedures and spectroscopic (¹H and ¹³C NMR) and analytical data of all compounds in Schemes 1 and 2. Chiral GC-methods for determination of ee and de of compounds 3 and 5. PDF (155K)

Article information

DOI: https://doi.org/10.1039/B419268K
Article type: Communication
Submitted: 23 Dec 2004
Accepted: 27 Jan 2005
First published: 09 Feb 2005

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Chem. Commun., 2005, 1387-1389

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Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones

R. P. van Summeren, S. J. W. Reijmer, B. L. Feringa and A. J. Minnaard, Chem. Commun., 2005, 1387 DOI: 10.1039/B419268K

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Chemical Communications

Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones†

Abstract

Supplementary files

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Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones

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