Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(18): 2844-2850
DOI: 10.1055/s-0034-1380921
DOI: 10.1055/s-0034-1380921
paper
Enantioselective Formation of Cyano-Bearing All-Carbon Quaternary Stereocenters: Copper-Catalyzed N-Arylation via Kinetic Resolution
Further Information
Publication History
Received: 23 March 2015
Accepted after revision: 30 April 2015
Publication Date:
29 June 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201518/lookinside/thumbnails/ss-2015-h0193-op_10-1055_s-0034-1380921-1.jpg)
Abstract
A copper-catalyzed enantioselective N-arylation for the formation of cyano-bearing all-carbon quaternary stereocenters was developed via kinetic resolution of racemic 3-amino-2-(2-iodobenzyl)propanenitriles. The reaction afforded the desired coupling products in moderate enantioselectivity under catalysis by CuI and a BINOL-derived ligand.
Key words
kinetic resolution - N-arylation - enantioselectivity - all-carbon quaternary stereocenters - copperSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380921.
- Supporting Information
-
References
- 1 Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis. Christoffers J, Baro A. Wiley-VCH; Weinheim: 2005
- 2a Fuji K. Chem. Rev. 1993; 93: 2037
- 2b Corey EJ, Guzman-Perez A. Angew. Chem. Int. Ed. 1998; 37: 388
- 2c Christoffers J, Mann A. Angew. Chem. Int. Ed. 2001; 40: 4591
- 2d Denissova I, Barriault L. Tetrahedron 2003; 59: 10105
- 2e Douglas CJ, Overman LE. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5363
- 2f Trost BM, Jiang C. Synthesis 2006; 369
- 2g Cozzi PG, Hilgraf R, Zimmermann N. Eur. J. Org. Chem. 2007; 5969
- 2h Bella M, Gasperi T. Synthesis 2009; 1583
- 2i Das JP, Marek I. Chem. Commun. 2011; 47: 4593
- 3a Mohr JT, Stoltz BM. Chem. Asian J. 2007; 2: 1476
- 3b Hong AY, Stoltz BM. Eur. J. Org. Chem. 2013; 2745
- 4 Corey EJ. Angew. Chem. Int. Ed. 2002; 41: 1650
- 5a Hawer C, Alexakis A. Chem. Commun. 2010; 46: 7295
- 5b Shintani R, Takeda M, Nishimura T, Hayashi T. Angew. Chem. Int. Ed. 2010; 49: 3969
- 5c Kikushima K, Holder JC, Gatti M, Stoltz BM. J. Am. Chem. Soc. 2011; 133: 6902
- 6a Akagawa K, Kudo K. Angew. Chem. Int. Ed. 2012; 51: 12786
- 6b Chen L.-A, Tang X, Xi J, Xu W, Gong L, Meggers E. Angew. Chem. Int. Ed. 2013; 52: 14021
- 6c Trost BM, Osipov M. Angew. Chem. Int. Ed. 2013; 52: 9176
- 6d Kastl R, Wennemers H. Angew. Chem. Int. Ed. 2014; 52: 7228
- 6e Chen Q, Wang G, Jiang X, Xu Z, Lin L, Wang R. Org. Lett. 2014; 16: 1394
- 6f Marek I, Minko Y, Pasco M, Mejuch T, Gilboa N, Chechik H, Das JP. J. Am. Chem. Soc. 2014; 136: 2682
- 7a Zhou F, Guo J, Liu J, Ding K, Yu S, Cai Q. J. Am. Chem. Soc. 2012; 134: 14326
- 7b Yang W, Long Y, Zhang S, Zeng Y, Cai Q. Org. Lett. 2013; 15: 3598
- 7c Yang W, Yan J, Long Y, Zhang S, Liu J, Zeng Y, Cai Q. Org. Lett. 2013; 15: 6022
- 7d Liu J, Yan J, Qin D, Cai Q. Synthesis 2014; 46: 1917
- 7e Zhou F, Cheng G.-J, Yang W, Long Y, Zhang S, Wu Y.-D, Zhang X, Cai Q. Angew. Chem. Int. Ed. 2014; 53: 9555
- 7f He N, Huo Y, Liu J, Huang Y, Zhang S, Cai Q. Org. Lett. 2015; 17: 374
- 8a Studer A, Schleth F. Synlett 2005; 3033
- 8b Rovis T In New Frontiers in Asymmetric Catalysis. Mikami K, Lautens M. Wiley; New York: 2007: 275-309
- 8c Atodiresei I, Schiffers I, Bolm C. Chem. Rev. 2007; 107: 5683
- 8d Díaz-de-Villegas MD, Gálvaz JA, Etayo P, Badorrey R, López-Ram-de-Víu MP. Chem. Eur. J. 2012; 18: 13920
For other selected examples for the construction of all-carbon quaternary stereocenters, see:
For selected reviews, see: