1 Rhodium- and Palladium-Catalyzed Asymmetric Conjugate Additions

作者: Guillaume Berthon , Tamio Hayashi

DOI: 10.1002/9783527630578.CH1

关键词:

摘要: Since the seminal report by Uemura [1] in 1995 for palladium, and Miyaura 1997 rhodium [2], late transition metal-catalyzed conjugate addition of organoboron reagents to activated alkenes has emerged as one most functional group-tolerant reliable carbon–carbon bond-forming processes. The maturity this methodology is such that it become an ideal testing ground new ligand concepts design, will be illustrated throughout chapter. A true statement robustness process application Rh-catalyzed enantioselective (ECA) on a kilogram-scale manufacture advanced pharmaceutical ingredients, its use key step synthesis complex natural products [3–5]. In chapter, overview provided – spanning from 2003 mid-2009 developments field rhodiumand palladium-catalyzed ECA organometallic (B, Si, Zn, Ti) alkenes. chapter not intended comprehensive, include only selected examples powerful methodology. For more in-depth comprehensive accounts, reader should consult number excellent reviews are available subject [6–16].

参考文章(246)
Pier Giorgio Cozzi, Robert Hilgraf, Nicole Zimmermann, Enantioselective Catalytic Formation of Quaternary Stereogenic Centers European Journal of Organic Chemistry. ,vol. 2007, pp. 5969- 5994 ,(2007) , 10.1002/EJOC.200700318
Krzysztof Plesniak, Andrzej Zarecki, Jerzy Wicha, The smiles rearrangement and the julia-kocienski olefination reaction. Topics in Current Chemistry. ,vol. 275, pp. 163- 250 ,(2006) , 10.1007/128_049
Toshinobu Korenaga, Kazutaka Osaki, Ryota Maenishi, Takashi Sakai, Electron-poor chiral diphosphine ligands: high performance for Rh-catalyzed asymmetric 1,4-addition of arylboronic acids at room temperature. Organic Letters. ,vol. 11, pp. 2325- 2328 ,(2009) , 10.1021/OL900719Z
Kazunori Kurihara, Noriyuki Sugishita, Kengo Oshita, Dongguo Piao, Yasunori Yamamoto, Norio Miyaura, Enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes Journal of Organometallic Chemistry. ,vol. 692, pp. 428- 435 ,(2007) , 10.1016/J.JORGANCHEM.2006.04.042
Takahiro Nishimura, Xun-Xiang Guo, Nanase Uchiyama, Taisuke Katoh, Tamio Hayashi, Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones. Journal of the American Chemical Society. ,vol. 130, pp. 1576- 1577 ,(2008) , 10.1021/JA710540S
Takahiro Nishimura, Sho Hirabayashi, Yuichi Yasuhara, Tamio Hayashi, Rhodium-catalyzed asymmetric hydroarylation of diphenylphosphinylallenes with arylboronic acids. Journal of the American Chemical Society. ,vol. 128, pp. 2556- 2557 ,(2006) , 10.1021/JA058763F
Christian Walter, Gertrud Auer, Martin Oestreich, Rhodium-catalyzed enantioselective conjugate silyl transfer: 1,4-addition of silyl boronic esters to cyclic enones and lactones. Angewandte Chemie. ,vol. 45, pp. 5675- 5677 ,(2006) , 10.1002/ANIE.200601747
Zhi-Qian Wang, Chen-Guo Feng, Ming-Hua Xu, Guo-Qiang Lin, Design of C2-symmetric tetrahydropentalenes as new chiral diene ligands for highly enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids. Journal of the American Chemical Society. ,vol. 129, pp. 5336- 5337 ,(2007) , 10.1021/JA0710914