Catalytic enantioselective addition of methyltriisopropoxititanium to aldehydes

作者: Marcos Veguillas , Ricard Solà , M. Ángeles Fernández-Ibañez , Beatriz Maciá

DOI: 10.1016/J.TETASY.2016.06.001

关键词:

摘要: An efficient catalyst for the enantioselective synthesis of chiral methyl carbinols from aldehydes is presented. The system uses methyltriisopropoxytitanium as a nucleophile and readily available binaphthyl derivative ligand. methylation both aromatic aliphatic proceeds with good yields high enantioselectivities under mild conditions.

参考文章(85)
Saul Patai, Frank R. Hartley, Carbon-carbon bond formation using organometallic compounds J. Wiley. ,(1985)
Witold Gładkowski, Andrzej Skrobiszewski, Marcelina Mazur, Monika Siepka, Agata Białońska, Convenient Chemoenzymatic Route to Optically Active β-Aryl-δ-iodo-γ- lactones and β-Aryl-γ-iodo-δ-lactones with the Defined Configurations of Stereogenic Centers European Journal of Organic Chemistry. ,vol. 2015, pp. 605- 615 ,(2015) , 10.1002/EJOC.201403343
Long-Sheng Zheng, Ke-Zhi Jiang, Yuan Deng, Xing-Feng Bai, Guang Gao, Feng-Lei Gu, Li-Wen Xu, Synthesis of Ar-BINMOL Ligands by [1,2]-Wittig Rearrangement to Probe Their Catalytic Activity in 1,2-Addition Reactions of Aldehydes with Grignard Reagents European Journal of Organic Chemistry. ,vol. 2013, pp. 748- 755 ,(2013) , 10.1002/EJOC.201201301
Thor H. Krane Thvedt, Tor Erik Kristensen, Eirik Sundby, Tore Hansen, Bård Helge Hoff, Enantioselectivity, swelling and stability of 4-hydroxyprolinol containing acrylic polymer beads in the asymmetric reduction of ketones Tetrahedron-asymmetry. ,vol. 22, pp. 2172- 2178 ,(2011) , 10.1016/J.TETASY.2011.12.001
Graham B. Jones, Robert S. Huber, Brant J. Chapman, Catalytic enantioselective synthesis of macrolides via asymmetric alkylation Tetrahedron-asymmetry. ,vol. 8, pp. 1797- 1809 ,(1997) , 10.1016/S0957-4166(97)00186-9
M. Lakshmi Kantam, Jagjit Yadav, Soumi Laha, Pottabathula Srinivas, Bojja Sreedhar, F. Figueras, Asymmetric hydrosilylation of ketones catalyzed by magnetically recoverable and reusable copper ferrite nanoparticles. Journal of Organic Chemistry. ,vol. 74, pp. 4608- 4611 ,(2009) , 10.1021/JO9002823
Toshiro Harada, Yuki Hiraoka, Takahiro Kusukawa, Yasuhisa Marutani, Shinichiro Matsui, Masashi Nakatsugawa, Koso Kanda, Phenylenebis(ethynyl)-Tethered Bis-BINOL Ligands for Enantioselective Catalyst Based on Dimeric Ti(IV) Aggregate Organic Letters. ,vol. 5, pp. 5059- 5062 ,(2003) , 10.1021/OL0360546
Gennaro Pescitelli, Lorenzo Di Bari, Piero Salvadori, Multiple Solution Species of Titanium(IV) 1,1‘-Bi-2-naphtholate Elucidated by NMR and CD Spectroscopy Organometallics. ,vol. 23, pp. 4223- 4229 ,(2004) , 10.1021/OM049709V
Tina Maria Konrad, Pascal Schmitz, Walter Leitner, Giancarlo Franciò, Highly enantioselective Rh-catalysed hydrogenation of 1-alkyl vinyl esters using phosphine-phosphoramidite ligands. Chemistry: A European Journal. ,vol. 19, pp. 13299- 13303 ,(2013) , 10.1002/CHEM.201303066