Angewandte Chemie International Edition in English

Volume 31, Issue 9 pp. 1190-1192

Communication

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trans-2-tert-Butylcyclohexanol, a Simple Selectively Optimized Cyclohexanol Auxiliary^†

Dipl.-Chem. Peter Esser,

Dipl.-Chem. Peter Esser

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

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Dr. Helmut Buschmann,

Dr. Helmut Buschmann

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

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Markus Meyer-Stork,

Markus Meyer-Stork

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

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Prof. Dr. Hans-Dieter Scharf,

Corresponding Author

Prof. Dr. Hans-Dieter Scharf

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)Search for more papers by this author

Dipl.-Chem. Peter Esser,

Dipl.-Chem. Peter Esser

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

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Dr. Helmut Buschmann,

Dr. Helmut Buschmann

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

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Markus Meyer-Stork,

Markus Meyer-Stork

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

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Prof. Dr. Hans-Dieter Scharf,

Corresponding Author

Prof. Dr. Hans-Dieter Scharf

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)

Institut für Organische Chemie der Technischen Hochschule, Prof.-Pirlet-Strasse 1, D-W-5100 Aachen (FRG)Search for more papers by this author

First published: September 1992

https://doi.org/10.1002/anie.199211901

Citations: 20

^†

This work was supported by the Deutsche Forschungsanstalt für Luft und Raumfahrt e.V, Hauptabteilung Energietechnik, Köln, der Deutsche Forschungsgemeinschaft, and the Fonds der Chemischen Industrie. We are grateful to Hüls AG (Marl) for supplying technical 2-tert-butylcyclohexanol. We also thank D. Gillmann for the synthetic work and S. Diebel for performing the GC analyses.

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Graphical Abstract

An economical auxiliary comparable to 8-phenylmenthol, trans-2-tert-butylcyclohexanol (1) was derived as a “structurally minimized” cyclohexanol with an optimized induction potential by application of the isoinversion principle and the structure–selectivity relationship of the cyclohexanol auxiliaries. A simple preparation of both enantiomers of 1 is possible on a large scale by the enzymatic saponification of a technical-grade product.

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Volume31, Issue9

September 1992

Pages 1190-1192

trans-2-tert-Butylcyclohexanol, a Simple Selectively Optimized Cyclohexanol Auxiliary^†

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trans-2-tert-Butylcyclohexanol, a Simple Selectively Optimized Cyclohexanol Auxiliary†

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trans-2-tert-Butylcyclohexanol, a Simple Selectively Optimized Cyclohexanol Auxiliary^†