New Practical Synthesis of the Exceptional Musk Odorants (R)-Muscone and (R,Z)-5-Muscenone

Authors

  • Oliver Knopff
  • Jérôme Kuhne

DOI:

https://doi.org/10.2533/chimia.2008.489

Keywords:

Aldol reaction, Amino alcohol, Asymmetric synthesis, Dynamic kinetic resolution, Elimination

Abstract

Herein we describe a short and practical synthesis of the exceptional musk odorants (R)-muscone and (R,Z)-5-muscenone from a readily available achiral macrocyclic diketone. The key step of the synthesis is the first sodium N-methylephedrate mediated enantioselective aldol condensation reaction (up to 76% ee). This new type of reaction proceeds via a dynamic kinetic resolution of an aldol intermediate.

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Published

2008-06-25

Issue

Vol. 62 No. 6 (2008): Chirality

Section

Scientific Articles

License

Copyright (c) 2008 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
O. Knopff, J. Kuhne, Chimia 2008, 62, 489, DOI: 10.2533/chimia.2008.489.