Synlett, Inhaltsverzeichnis Synlett 2014; 25(5): 736-740DOI: 10.1055/s-0033-1340628 letter © Georg Thieme Verlag Stuttgart · New York Nickel(0)-Promoted Carboxylation of Allenamides with Carbon Dioxide via a Nickelalactone Intermediate Nozomi Saito* a Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan Fax: +81(11)7064982 eMail: biyo@pharm.hokudai.ac.jp , Yasuyuki Sugimura a Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan Fax: +81(11)7064982 eMail: biyo@pharm.hokudai.ac.jp , Yoshihiro Sato* a Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan Fax: +81(11)7064982 eMail: biyo@pharm.hokudai.ac.jp b ACT-C, Japan Science and Technology Agency (JST), Sapporo 060-0812, Japan › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Nickel(0)-promoted carboxylation of N-allenylamides (allenamides) with carbon dioxide proceeded via a nickelalactone intermediate to give β-amino acid derivatives. It was also found that the regioselectivity at the oxidative addition stage was strongly affected by the substituents on the allene part. Key words Key wordsnickel - allenamide - carbon dioxide - fixation - β-amino acid Volltext Referenzen References and Notes For reviews on transition-metal-promoted carboxylation, see: 1a Braunstein P, Matt D, Nobel D. Chem. Rev. 1988; 88: 747 1b Gibson DH. Chem. Rev. 1996; 96: 2063 1c Yin X, Moss JR. Coord. Chem. Rev. 1999; 181: 27 1d Sakakura T, Choi J.-C, Yasuda H. Chem. Rev. 2007; 107: 2365 1e Hou Z, Ohishi T In Comprehensive Organometallic Chemistry III . Vol. 10. Crabtree RH, Mingos DM. P, Ojima I. Elsevier; Oxford: 2007: 537-555 1f Correa A, Martín R. Angew. Chem. Int. Ed. 2009; 48: 6201 1g Riduan SN, Zhang Y. Dalton Trans. 2010; 39: 3347 1h Mikkelsen M, Jørgensen M, Krebs FC. Energy Environ. Sci. 2010; 3: 43 1i Huang K, Sun C.-L, Shi Z.-J. Chem. Soc. Rev. 2011; 40: 2435 1j Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kühn FE. Angew. Chem. Int. Ed. 2011; 50: 8510 1k Martín R, Kleij AW. ChemSusChem 2011; 4: 1259 1l Tsuji Y, Fujihara T. Chem. Commun. 2012; 48: 9956 1m Omae I. Coord. Chem. Rev. 2012; 256: 1384 For the most recent selected examples of transition-metal-promoted carboxylations, see: 2a Tran-Vu H, Daugulis O. ACS Catal. 2013; 3: 2417 2b Takimoto M, Hou Z. Chem. Eur. J. 2013; 19: 11439 2c Yu B, Diao Z.-F, Guo C.-X, Zhong C.-L, He L.-N, Zhao Y.-N, Song Q.-W, Liu A.-H, Wang J.-Q. Green Chem. 2013; 15: 2401 2d León T, Correa A, Martin R. J. Am. Chem. Soc. 2013; 135: 1221 2e Sasano K, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2013; 135: 10954 2f Feng X, Sun A, Zhang S, Yu X, Bao M. Org. Lett. 2013; 15: 108 2g Duong HA, Huleatt PB, Tan Q.-W, Shuying EL. Org. Lett. 2013; 15: 4034 2h Hase S, Kayaki Y, Ikariya T. Organometallics 2013; 32: 5285 ; see also ref. 1l 3 For a review on nickel-mediated or -catalyzed carboxylation via nickelalactone, see: Takimoto M, Mori M. In Modern Organonickel Chemistry . Tamaru Y. Wiley-VCH; Weinheim: 2005: 205-223 4a Saito S, Nakagawa S, Koizumi T, Hirayama K, Yamamoto Y. J. Org. Chem. 1999; 64: 3975 4b Takimoto M, Shimizu K, Mori M. Org. Lett. 2001; 3: 3345 4c Shimizu K, Takimoto M, Mori M. Org. Lett. 2003; 5: 2323 4d Aoki M, Kaneko M, Izumi S, Ukai K, Iwasawa N. Chem. Commun. 2004; 2568 4e Shimizu K, Takimoto M, Sato Y, Mori M. Org. Lett. 2005; 7: 195 4f Langer J, Görls H, Walther D. Polyhedron 2012; 32: 60 5a Takimoto M, Mori M. J. Am. Chem. Soc. 2001; 123: 2895 5b Takimoto M, Nakamura Y, Kimura K, Mori M. J. Am. Chem. Soc. 2004; 126: 5956 6a Takimoto M, Kawamura M, Mori M. Org. Lett. 2003; 5: 2599 6b Takimoto M, Kawamura M, Mori M. Synthesis 2004; 791 6c Takimoto M, Kawamura M, Mori M, Sato Y. Synlett 2005; 2019 6d Aoki M, Izumi S, Kaneko M, Ukai K, Takaya J, Iwasawa N. Org. Lett. 2007; 9: 1251 6e Takimoto M, Kawamura M, Mori M, Sato Y. Synlett 2011; 1423 7a Louie J, Gibby JE, Farnworth MV, Tekavec TN. J. Am. Chem. Soc. 2002; 124: 15188 7b Tekavec TN, Arif AM, Louie J. Tetrahedron 2004; 60: 7431 8a Takimoto M, Mizuno T, Sato Y, Mori M. Tetrahedron Lett. 2005; 46: 5173 8b Takimoto M, Mizuno T, Mori M, Sato Y. Tetrahedron 2006; 62: 7589 8c Mizuno T, Oonishi Y, Takimoto M, Sato Y. Eur. J. Org. Chem. 2011; 2606 For leading reviews on the chemistry of allenamide, see: 9a Wei L.-L, Xiong H, Hsung RP. Acc. Chem. Res. 2003; 36: 773 9b Lu T, Lu Z, Ma Z.-X, Zhang Y, Hsung RP. Chem. Rev. 2013; 113: 4862 10 It is known that oxidative cycloaddition of allene and a CO2 to a zero-valent nickel center proceeded in a regioselective manner to give α-alkylidenenickelalactone, see: Hoberg H, Oster BW. J. Organomet. Chem. 1984; 266: 321 11 The regio- and stereochemistry of the carboxylation compound was determined by NOE experiments, see the Supporting Information. Zusatzmaterial Zusatzmaterial Supporting Information
