Topics in Current Chemistry (2019) 377:38
1 3
7 Conclusion
To date, the chemical community has witnessed the fruitful growth of the powerful strategy of combining enamine and transition metal catalysis. Starting from the
first examples in 2006, demonstrating the possibility of overcoming any inhibition
or quenching by concomitantly merging simple amine catalysts, providing nucleophilic enamine coupled with transition metal activated electrophilic intermediate.
Endeavors to further expand the strategy have allowed a plethora of novel chemical
reactions with a wide range of simple starting materials to proceed in atom- and
step-economic manner. Furthermore, we have seen novel strategies adopting the
stereodivergent preparation of a wide range of important compounds with multiple
stereocenters and with diversified functionalities, which additionally expands the
chemical space. We believe this strategy will continue emerging into new innovative reactions allowing the coupling of more challenging components with indefinite
chemical transformations.
Acknowledgements Open access funding provided by Mid Sweden University.
Open Access This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creat iveco mmons .org/licen ses/by/4.0/), which permits unrestricted use, distribution,
and reproduction in any medium, provided you give appropriate credit to the original author(s) and the
source, provide a link to the Creative Commons license, and indicate if changes were made.
References
1. Dalko PI, Moisan L (2001) Enantioselective organocatalysis. Angew Chem Int Ed
40(20):3726–3748
2. MacMillan DWC (2008) The advent and development of organocatalysis. Nature
455(7211):304–308
3. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Asymmetric enamine catalysis. Chem Rev
107(12):5471–5569
4. Erkkilä A, Majander I, Pihko PM (2007) Iminium catalysis. Chem Rev 107(12):5416–5470
5. Afewerki S, Córdova A (2016) Combinations of aminocatalysts and metal catalysts: a powerful
cooperative approach in selective organic synthesis. Chem Rev 116(22):13512–13570
6. Wang H, Deng Y (2015) Cooperative enamine-lewis acid catalysis. In: Peters R (ed) Cooperative
catalysis. Wiley-VCH, Weinheim, pp 111–144
7. Afewerki S, Córdova A (2017) Cooperative lewis acids and aminocatalysis. In: Mlynarski J (ed)
Chiral lewis acids in organic synthesis. Wiley-VCH, Weinheim, pp 345–374
8. Trost BM, Van Vranken DL (1996) Asymmetric transition metal-catalyzed allylic alkylations.
Chem Rev 96(12):395–422
9. Lauterbach T, Asiri AM, Hashmi ASK (2014) Advances in organmetallic intermediates of gold
catalysis. In: Pérez PJ (ed) Advances in organometallic chemistry, vol 62. Academic Press, Cambridge, pp 261–297
10. Afewerki S, Breistein P, Pirttilä K, Deiana L, Dziedzic P, Ibrahem I, Córdova A (2012) Catalytic enantioselective β-alkylation of & #x03B1;, β-unsaturated aldehydes by combination of
transition-metal- and aminocatalysis: total synthesis of bisabolane sesquiterpenes. Chem Eur J
17(32):8784–8788
11. Deng Y, Kumar S, Wang H (2014) Synergistic-cooperative combination of enamine catalysis with
transition metal catalysis. Chem Commun 50:4272–4284
12. Ibrahem I, Córdova A (2006) Direct catalytic intermolecular α-allylic alkylation of aldehydes by
combination of transition-metal and organocatalysis. Angew Chem Int Ed 45(12):1952–1956
Reprinted from the journal
22
1 3
7 Conclusion
To date, the chemical community has witnessed the fruitful growth of the powerful strategy of combining enamine and transition metal catalysis. Starting from the
first examples in 2006, demonstrating the possibility of overcoming any inhibition
or quenching by concomitantly merging simple amine catalysts, providing nucleophilic enamine coupled with transition metal activated electrophilic intermediate.
Endeavors to further expand the strategy have allowed a plethora of novel chemical
reactions with a wide range of simple starting materials to proceed in atom- and
step-economic manner. Furthermore, we have seen novel strategies adopting the
stereodivergent preparation of a wide range of important compounds with multiple
stereocenters and with diversified functionalities, which additionally expands the
chemical space. We believe this strategy will continue emerging into new innovative reactions allowing the coupling of more challenging components with indefinite
chemical transformations.
Acknowledgements Open access funding provided by Mid Sweden University.
Open Access This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creat iveco mmons .org/licen ses/by/4.0/), which permits unrestricted use, distribution,
and reproduction in any medium, provided you give appropriate credit to the original author(s) and the
source, provide a link to the Creative Commons license, and indicate if changes were made.
References
1. Dalko PI, Moisan L (2001) Enantioselective organocatalysis. Angew Chem Int Ed
40(20):3726–3748
2. MacMillan DWC (2008) The advent and development of organocatalysis. Nature
455(7211):304–308
3. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Asymmetric enamine catalysis. Chem Rev
107(12):5471–5569
4. Erkkilä A, Majander I, Pihko PM (2007) Iminium catalysis. Chem Rev 107(12):5416–5470
5. Afewerki S, Córdova A (2016) Combinations of aminocatalysts and metal catalysts: a powerful
cooperative approach in selective organic synthesis. Chem Rev 116(22):13512–13570
6. Wang H, Deng Y (2015) Cooperative enamine-lewis acid catalysis. In: Peters R (ed) Cooperative
catalysis. Wiley-VCH, Weinheim, pp 111–144
7. Afewerki S, Córdova A (2017) Cooperative lewis acids and aminocatalysis. In: Mlynarski J (ed)
Chiral lewis acids in organic synthesis. Wiley-VCH, Weinheim, pp 345–374
8. Trost BM, Van Vranken DL (1996) Asymmetric transition metal-catalyzed allylic alkylations.
Chem Rev 96(12):395–422
9. Lauterbach T, Asiri AM, Hashmi ASK (2014) Advances in organmetallic intermediates of gold
catalysis. In: Pérez PJ (ed) Advances in organometallic chemistry, vol 62. Academic Press, Cambridge, pp 261–297
10. Afewerki S, Breistein P, Pirttilä K, Deiana L, Dziedzic P, Ibrahem I, Córdova A (2012) Catalytic enantioselective β-alkylation of & #x03B1;, β-unsaturated aldehydes by combination of
transition-metal- and aminocatalysis: total synthesis of bisabolane sesquiterpenes. Chem Eur J
17(32):8784–8788
11. Deng Y, Kumar S, Wang H (2014) Synergistic-cooperative combination of enamine catalysis with
transition metal catalysis. Chem Commun 50:4272–4284
12. Ibrahem I, Córdova A (2006) Direct catalytic intermolecular α-allylic alkylation of aldehydes by
combination of transition-metal and organocatalysis. Angew Chem Int Ed 45(12):1952–1956
Reprinted from the journal
22