Contribution in an anthology

Appeared in: Comprehensive Organic Synthesis, Volume 6, Heteroatom manipulation

Editor list: Knochel, Paul; Molander, Gary A.; Burke, Steven

Publication year: 2014

Pages: 354-

ISBN: 978-0-08-099959-3

DOI Link: https://doi.org/10.1016/B978-0-08-097742-3.00611-X

Edition: 2. edition

Abstract: 

Acyl transfer reactions are one of the most common transformations in organic synthesis as well as in nature. Though many methods (acidic catalysis, basic catalysis, and nucleophilic catalysis, e.g., 4-dimethylaminopyridine) for the acylation of alcohols have been known for centuries, asymmetric approaches were just realized in the last 15-20 years. Asymmetric acyl transfer onto alcohols presents a powerful tool for the synthesis of enantiopure substrates, which are important building blocks for the synthesis of natural products, pharmaceuticals, and chiral ligands. The introduction explains the differences between kinetic resolution, dynamic kinetic resolution, and desymmetrization and shows how the catalytic efficacy of a kinetic resolution is typically expressed (Kagan's equation). This article summarizes organocatalysts and metal-complexes capable of an enantioselective acyl transfer. Substrate scope, reaction conditions, selectivities, mechanism, and the accessibility of the catalysts are organized by type of catalyst. The performances of the catalysts are discussed and, if possible, comparisons toward efficiency are made. Additionally, examples for the utilization of chiral acylation catalysts in natural product synthesis are presented in each section. © 2014 Elsevier Ltd. All rights reserved.

Harvard Citation style: Zell, D. and Schreiner, P. (2014) Acylation-Type Reactions: Synthesis of Esters via Acyl Transfer, in Knochel, P., Molander, G. and Burke, S. (eds.) Comprehensive Organic Synthesis, Volume 6, Heteroatom manipulation. 2. edition. Amsterdam: Elsevier, p. 354. https://doi.org/10.1016/B978-0-08-097742-3.00611-X

APA Citation style: Zell, D., & Schreiner, P. (2014). Acylation-Type Reactions: Synthesis of Esters via Acyl Transfer. In Knochel, P., Molander, G., & Burke, S. (Eds.), Comprehensive Organic Synthesis, Volume 6, Heteroatom manipulation (2. edition, p. 354). Elsevier. https://doi.org/10.1016/B978-0-08-097742-3.00611-X