Vol.:(0123456789)
Topics in Current Chemistry (2020) 378:16
https://doi.org/10.1007/s41061-020-0279-7
1 3
REVIEW
Tertiary Amine Lewis Base Catalysis in Combination
with Transition Metal Catalysis
Gary J. Knox
1
· Luke S. Hutchings‑Goetz
1
· Colin M. Pearson
1
·
Thomas N. Snaddon
1
Received: 23 September 2019 / Accepted: 2 January 2020 / Published online: 16 January 2020
© Springer Nature Switzerland AG 2020
Abstract
The cooperation between two orthogonal catalytic events during the formation of
carbon–carbon and carbon–heteroatom bonds has emerged as an effective strategy for enantioselective chemical synthesis. In recent years, a number of pioneering investigations have described useful chemical synthesis methods whereby the
reactivity or nucleophile–electrophile combinations can be fine-tuned or extended
far beyond the effect and influence of a single catalyst. The recognition of this has
had profound implications for the development cooperative catalysis as a field and
has provided a foundation for the development of broadly useful chemical synthesis methods. This chapter focuses on the combination of tertiary amine Lewis base
and transition metal catalysts, which the authors hope will simulate further developments and advances.
Keywords Cooperative catalysis · Lewis base · Tertiary amine · Transition metal
1 Introduction
Transition metal catalysis is a vital technology for the chemical synthesis of important and valuable organic molecules [1]. This is largely due to the reliability, predictability, and modularity of transition metal complexes. More recently, organocatalysis has emerged as a similarly powerful and often complementary reactivity
platform [for relevant reviews, see 2–4]. However, while both are undoubtedly mainstays of the synthesis armory, efforts to expand to regions of inaccessible reactivity
* Thomas N. Snaddon
tsnaddon@indiana.edu
1
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington,
IN 47405, USA
Reprinted from the journal
99
Chapter 5 was originally published as Knox, G. J., Hutchings‑Goetz, L. S., Pearson, C. M. & Snaddon, T. N.
Topics in Current Chemistry (2020) 378: 16. https://doi.org/10.1007/s41061-020-0279-7.
Topics in Current Chemistry (2020) 378:16
https://doi.org/10.1007/s41061-020-0279-7
1 3
REVIEW
Tertiary Amine Lewis Base Catalysis in Combination
with Transition Metal Catalysis
Gary J. Knox
1
· Luke S. Hutchings‑Goetz
1
· Colin M. Pearson
1
·
Thomas N. Snaddon
1
Received: 23 September 2019 / Accepted: 2 January 2020 / Published online: 16 January 2020
© Springer Nature Switzerland AG 2020
Abstract
The cooperation between two orthogonal catalytic events during the formation of
carbon–carbon and carbon–heteroatom bonds has emerged as an effective strategy for enantioselective chemical synthesis. In recent years, a number of pioneering investigations have described useful chemical synthesis methods whereby the
reactivity or nucleophile–electrophile combinations can be fine-tuned or extended
far beyond the effect and influence of a single catalyst. The recognition of this has
had profound implications for the development cooperative catalysis as a field and
has provided a foundation for the development of broadly useful chemical synthesis methods. This chapter focuses on the combination of tertiary amine Lewis base
and transition metal catalysts, which the authors hope will simulate further developments and advances.
Keywords Cooperative catalysis · Lewis base · Tertiary amine · Transition metal
1 Introduction
Transition metal catalysis is a vital technology for the chemical synthesis of important and valuable organic molecules [1]. This is largely due to the reliability, predictability, and modularity of transition metal complexes. More recently, organocatalysis has emerged as a similarly powerful and often complementary reactivity
platform [for relevant reviews, see 2–4]. However, while both are undoubtedly mainstays of the synthesis armory, efforts to expand to regions of inaccessible reactivity
* Thomas N. Snaddon
tsnaddon@indiana.edu
1
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington,
IN 47405, USA
Reprinted from the journal
99
Chapter 5 was originally published as Knox, G. J., Hutchings‑Goetz, L. S., Pearson, C. M. & Snaddon, T. N.
Topics in Current Chemistry (2020) 378: 16. https://doi.org/10.1007/s41061-020-0279-7.