Alkene carboamination information

Alkene carboamination is the simultaneous formation of C–N and C–C bonds across an alkene. This method represents a powerful strategy to build molecular complexity with up to two stereocenters in a single operation. Generally, there are four categories of reaction modes for alkene carboamination.^[1]^[2]^[3]^[4] The first class is cyclization reactions, which will form a N-heterocycle as a result. The second class has been well established in the last decade. Alkene substrates with a tethered nitrogen nucleophile have been used in these transformations to promote intramolecular aminocyclization.^[5]^[6] While intermolecular carboamination is extremely hard, people have developed a strategy to combine the nitrogen and carbon part, which is known as the third class. The most general carboamination, which takes three individual parts and couples them together is still underdeveloped.

^ Coldham, I.; Hufton, R. (2005). "Intramolecular dipolar cycloaddition reactions of azomethine ylides". Chem. Rev. 105 (7): 2765–2810. doi:10.1021/cr040004c. PMID 16011324.
^ Nakamura, I.; Yamamoto, Y. (2004). "Transition-metal-catalyzed reactions in heterocyclic synthesis". Chem. Rev. 104 (5): 2127–2198. doi:10.1021/cr020095i. PMID 15137788. S2CID 39798353.
^ Wolfe, J. P. (2006). "Palladium-catalyzed carboetherification and carboamination reactions of γ-hydroxy- and γ-aminoalkenes for the synthesis of tetrahydrofurans and pyrrolidines". Eur. J. Org. Chem. 2007 (4): 571–582. doi:10.1002/ejoc.200600767. PMC 2633094. PMID 19183704.
^ Piou, T.; Rovis, T. (2015). "Rhodium-catalysed syn-carboamination of alkenes via a transient directing group". Nature. 527 (7576): 86–90. Bibcode:2015Natur.527...86P. doi:10.1038/nature15691. PMC 4636455. PMID 26503048.
^ Ney, J. E.; Wolfe, J. P. (2004). "Palladium-catalyzed synthesis of N-aryl pyrrolidines from γ-(N-arylamino) alkenes: evidence for chemoselective alkene insertion into Pd–N bonds". Angew. Chem. Int. Ed. 43 (27): 3605–3608. doi:10.1002/anie.200460060. PMID 15293259.
^ Lira, R.; Wolfe, J. P. (2004). "Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification". J. Am. Chem. Soc. 126 (43): 13906–13907. doi:10.1021/ja0460920. PMID 15506735.

[1] Coldham, I.; Hufton, R. (2005). "Intramolecular dipolar cycloaddition reactions of azomethine ylides". Chem. Rev. 105 (7): 2765–2810. doi:10.1021/cr040004c. PMID 16011324.

[2] Nakamura, I.; Yamamoto, Y. (2004). "Transition-metal-catalyzed reactions in heterocyclic synthesis". Chem. Rev. 104 (5): 2127–2198. doi:10.1021/cr020095i. PMID 15137788. S2CID 39798353.

[3] Wolfe, J. P. (2006). "Palladium-catalyzed carboetherification and carboamination reactions of γ-hydroxy- and γ-aminoalkenes for the synthesis of tetrahydrofurans and pyrrolidines". Eur. J. Org. Chem. 2007 (4): 571–582. doi:10.1002/ejoc.200600767. PMC 2633094. PMID 19183704.

[4] Piou, T.; Rovis, T. (2015). "Rhodium-catalysed syn-carboamination of alkenes via a transient directing group". Nature. 527 (7576): 86–90. Bibcode:2015Natur.527...86P. doi:10.1038/nature15691. PMC 4636455. PMID 26503048.

[5] Ney, J. E.; Wolfe, J. P. (2004). "Palladium-catalyzed synthesis of N-aryl pyrrolidines from γ-(N-arylamino) alkenes: evidence for chemoselective alkene insertion into Pd–N bonds". Angew. Chem. Int. Ed. 43 (27): 3605–3608. doi:10.1002/anie.200460060. PMID 15293259.

[6] Lira, R.; Wolfe, J. P. (2004). "Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification". J. Am. Chem. Soc. 126 (43): 13906–13907. doi:10.1021/ja0460920. PMID 15506735.

Alkene carboamination information

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Alkene carboamination

Dialkylbiaryl phosphine ligands