pp 1-59 | Cite as

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

Chapter
Part of the Topics in Heterocyclic Chemistry book series

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.

Keywords

Asymmetric synthesis Aza camphor Camphor Camphor-derived lactam Pinene Stereoselective Terpenes 

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Copyright information

© Springer International Publishing AG 2018

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of RochesterRochesterUSA
  2. 2.School of Chemistry and Materials ScienceRIT College of ScienceRochesterUSA

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