Synthesis of Chiral Tertiary Alcohols by Cu(I) -Catalyzed Enantioselective Addition of Organomagnesium Reagents to Ketones.

作者: Jiawei Rong , Tilde Pellegrini , Syuzanna R. Harutyunyan

DOI: 10.1002/CHEM.201503412

关键词:

摘要: Catalytic enantioselective addition of organometallic nucleophiles to ketones is among the most straightforward approaches synthesis chiral tertiary alcohols. The first such catalytic methodologies using highly reactive organomagnesium reagents, which are preferred reagents in terms cost, availability, atom efficiency, and structural diversity, were developed only during last five years. This Concept article highlights fundamental breakthrough that made development for Cu(I) -catalyzed alkylation possible.

参考文章(123)
Kei Takeda, Yuji Ohnishi, Toru Koizumi, Enantioselective Reduction of α,β-Unsaturated Acylsilanes by Chiral Lithium Amides Organic Letters. ,vol. 1, pp. 237- 240 ,(1999) , 10.1021/OL990574C
Eiichi Nakamura, Seiji Mori, Keiji Morokuma, Reaction Pathway of the Conjugate Addition of Lithium Organocuprate Clusters to Acrolein Journal of the American Chemical Society. ,vol. 119, pp. 4900- 4910 ,(1997) , 10.1021/JA964209H
Diego J. Ramón, Miguel Yus, FIRST ENANTIOSELECTIVE ADDITION OF DIALKYLZINC TO KETONES PROMOTED BY TITANIUM(IV) DERIVATIVES Tetrahedron Letters. ,vol. 39, pp. 1239- 1242 ,(1998) , 10.1016/S0040-4039(97)10765-1
Sang-Jin Jeon, Hongmei Li, Celina García, Lynne K. LaRochelle, Patrick J. Walsh, Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones. Journal of Organic Chemistry. ,vol. 70, pp. 448- 455 ,(2005) , 10.1021/JO048683E
Steven H. Bertz, Richard A. Hardin, Thomas J. Heavey, Craig A. Ogle, The X‐ray Crystal Structure of a Cuprate–Carbonyl π‐Complex Angewandte Chemie. ,vol. 52, pp. 10250- 10252 ,(2013) , 10.1002/ANIE.201303783
R. Oost, J. Rong, A. J. Minnaard, S. R. Harutyunyan, Synthesis of new derivatives of copper complexes of Josiphos family ligands for applications in asymmetric catalysis Catalysis Science & Technology. ,vol. 4, pp. 1997- 2005 ,(2014) , 10.1039/C4CY00180J
Francesca Caprioli, Ashoka V. R. Madduri, Adriaan J. Minnaard, Syuzanna R. Harutyunyan, Asymmetric amplification in the catalytic enantioselective 1,2-addition of Grignard reagents to enones Chemical Communications. ,vol. 49, pp. 5450- 5452 ,(2013) , 10.1039/C3CC41892H