Cobalt-Catalyzed Asymmetric Sequential Hydroboration/Hydrogenation of Internal Alkynes

作者: Jun Guo , Biao Cheng , Xuzhong Shen , Zhan Lu

DOI: 10.1021/JACS.7B09832

关键词:

摘要: A highly regio- and enantioselective cobalt-catalyzed hydroboration/hydrogenation of internal alkynes with HBpin a hydrogen balloon in one pot was developed. new type chiral imidazoline iminopyridine (IIP) ligand introduced for the first time this novel efficient strategy. This protocol used relatively simple available starting materials good functional group tolerance to construct more valuable secondary organoboronates. The primary mechanistic studies illustrated that regioselective hydroboration did initially occur followed by HBpin-promoted hydrogenation alkenylboronates.

参考文章(53)
David H. Woodmansee, Andreas Pfaltz, Iridium-Catalyzed Asymmetric Hydrogenation of Olefins with Chiral N,P and C,N Ligands Iron Catalysis: Fundamentals and Applications. ,vol. 34, pp. 31- 76 ,(2011) , 10.1007/978-3-642-15334-1_3
Donald S. Matteson, .alpha.-Halo boronic esters: intermediates for stereodirected synthesis Chemical Reviews. ,vol. 89, pp. 1535- 1551 ,(1989) , 10.1021/CR00097A009
Klas Källström, Ian Munslow, Pher G. Andersson, Ir‐Catalysed Asymmetric Hydrogenation: Ligands, Substrates and Mechanism Chemistry: A European Journal. ,vol. 12, pp. 3194- 3200 ,(2006) , 10.1002/CHEM.200500755
Cathleen M. Crudden, Ben W. Glasspoole, Christopher J. Lata, Expanding the scope of transformations of organoboron species: carbon-carbon bond formation with retention of configuration. Chemical Communications. pp. 6704- 6716 ,(2009) , 10.1039/B911537D
Masato Ueda, Atsushi Saitoh, Norio Miyaura, Asymmetric hydrogenation of 1-phenylethenylboronic acid and esters for the synthesis of chiral organoboron compounds Journal of Organometallic Chemistry. ,vol. 642, pp. 145- 147 ,(2002) , 10.1016/S0022-328X(01)01239-6
Jianhui Chen, Tuo Xi, Xiang Ren, Biao Cheng, Jun Guo, Zhan Lu, Asymmetric cobalt catalysts for hydroboration of 1,1-disubstituted alkenes Organic chemistry frontiers. ,vol. 1, pp. 1306- 1309 ,(2014) , 10.1039/C4QO00295D
Sean M. Smith, Nathan C. Thacker, James M. Takacs, Efficient amide-directed catalytic asymmetric hydroboration. Journal of the American Chemical Society. ,vol. 130, pp. 3734- 3735 ,(2008) , 10.1021/JA710492Q
Javier Mazuela, Per-Ola Norrby, Pher G. Andersson, Oscar Pàmies, Montserrat Diéguez, Pyranoside phosphite-oxazoline ligands for the highly versatile and enantioselective ir-catalyzed hydrogenation of minimally functionalized olefins. A combined theoretical and experimental study. Journal of the American Chemical Society. ,vol. 133, pp. 13634- 13645 ,(2011) , 10.1021/JA204948K
Herbert C. Brown, P. Veeraraghavan Ramachandran, Versatile α-pinene-based borane reagents for asymmetric syntheses Journal of Organometallic Chemistry. ,vol. 500, pp. 1- 19 ,(1995) , 10.1016/0022-328X(95)00509-O