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Synthesis and Utility of Heteroand Non-heterocyclic Chiral Auxiliaries Derived from Terpenes: Camphor and Pinene

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Book cover Heterocycles as Chiral Auxiliaries in Asymmetric Synthesis

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 55))

Abstract

This chapter reviews the literature through the end of 2016 directed to the preparation and use of heterocyclic chiral auxiliaries derived for terpenes, principally camphor, borneol (via ent-camphor), and pinene. Since they are closely aligned in their utility, the scope of this chapter was expanded somewhat to include non-heterocyclic chiral auxiliaries derived from these terpenes where relevant and appropriate. The chapter is organized by auxiliary, and within the section on a given auxiliary are subsections on preparation and the various applications of that auxiliary to asymmetric synthesis organized generally by reaction type. A wide variety of applications are reviewed including cycloadditions, condensations, sigmatropic rearrangements, alkylations, and acylations to name a few. While the chapter is not intended to be comprehensive, it is intended to give the reader the scope and breadth of the structural types of auxiliaries derived from camphor, borneol, and pinene and their applications to asymmetric synthesis.

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Author information

Authors and Affiliations

  1. Department of Chemistry, University of Rochester, Rochester, NY, USA

    Robert K. Boeckman Jr.

  2. School of Chemistry and Materials Science, RIT College of Science, Rochester, NY, USA

    Jeremy A. Cody

Authors
  1. Robert K. Boeckman Jr.
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  2. Jeremy A. Cody
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Corresponding authors

Correspondence to Robert K. Boeckman Jr. or Jeremy A. Cody .

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Editors and Affiliations

  1. Institute of Organic and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf, Germany

    Manfred Braun

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Boeckman, R.K., Cody, J.A. (2018). Synthesis and Utility of Heteroand Non-heterocyclic Chiral Auxiliaries Derived from Terpenes: Camphor and Pinene. In: Braun, M. (eds) Heterocycles as Chiral Auxiliaries in Asymmetric Synthesis. Topics in Heterocyclic Chemistry, vol 55. Springer, Cham. https://doi.org/10.1007/7081_2017_12

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