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 2013; 45(4): 527-535
DOI: 10.1055/s-0032-1316847
DOI: 10.1055/s-0032-1316847
paper
A Scalable Synthesis of Chiral Modular Phosphine–Phosphite Ligands
Further Information
Publication History
Received: 17 October 2012
Accepted after revision: 24 December 2012
Publication Date:
18 January 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201304/lookinside/thumbnails/10.1055-s-0032-1316847-1.jpg)
Abstract
The outstanding usefulness of phenol-derived chiral phosphine–phosphite ligands has recently been shown in a number of transition-metal-catalyzed C–C bond-forming reactions. This is exemplified by the synthesis of five new ligands in an optimized procedure that can be reliably performed on a multigram scale.
Key words
Chiral P,P-ligands - enantioselective catalysis - bromine–lithium exchange - synthetic methods - asymmetric 1,4-additionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 M. Dindaroğlu and A. Falk contributed equally to this work.
- 2a Comprehensive Asymmetric Catalysis. Jacobsen EN, Pfaltz A, Yamamoto H. Vol. 1-3. Berlin: Springer; 1999
- 2b Busacca CA, Fandrick DR, Song JJ, Senanayakea CH. Adv. Synth. Catal. 2011; 353: 1825
- 3a Noyori R, Takaya H. Acc. Chem. Res. 1990; 23: 345
- 3b Nozaki K, Sakai N, Nanno T, Higashijima T, Mano S, Horiushi T, Takaya H. J. Am. Chem. Soc. 1997; 119: 4413
-
4a Togni A. Angew. Chem., Int. Ed. Engl. 1996; 35: 1475 ; Angew. Chem.
1996, 108, 1581
-
4b Ireland T, Grossheimann G, Wieser-Jeunesse C, Knochel P. Angew. Chem. Int. Ed. 1999; 38: 3212 ; Angew. Chem. 1999, 111, 3397
- 5a Kranich R, Eis K, Geis O, Mühle S, Bats JW, Schmalz H.-G. Chem. Eur. J. 2000; 6: 2874
- 5b Yoon TP, Jacobsen EN. Science 2003; 299: 1691
- 6a Fernández-Pérez H, Etayo P, Panossian A, Vidal-Ferran A. Chem. Rev. 2011; 111: 2119
- 6b Lühr S, Holz J, Börner A. ChemCatChem 2011; 3: 1708
- 7a Blume F, Zemolka S, Fey T, Kranich R, Schmalz H.-G. Adv. Synth. Catal. 2002; 344: 868
- 7b Velder J, Robert T, Weidner I, Neudörfl J.-M, Lex J, Schmalz H.-G. Adv. Synth. Catal. 2008; 350: 1309
- 8 In our first-generation synthesis (ref. 6a), unprotected ortho-phosphanylphenols were used as intermediates, which proved to be highly air-sensitive
- 9a Beck AK, Bastani B, Plattner DA, Petter W, Seebach D, Braunschweiger H, Gysi P, La Vecchia L. Chimia 1991; 45: 238
- 9b Beck AK, Gysi P, La Vecchia L, Seebach D. Org. Synth., Coll. Vol. X 2004; 76: 349
- 10a Brunel JM. Chem. Rev. 2005; 105: 857 ; Chem. Rev. 2005, 105, 4233 (addendum/corrigendum) For an update, see: Brunel J. M.; Chem. Rev.; 2007, 107: 1
- 11 Bhowmick KC, Joshi NN. Tetrahedron: Asymmetry 2006; 17: 1901
- 12 Werle S, Fey T, Neudörfl J.-M, Schmalz H.-G. Org. Lett. 2007; 9: 3555
- 13a Robert T, Velder J, Schmalz H.-G. Angew. Chem. Int. Ed. 2008; 47: 7718
- 13b Naeemi Q, Robert T, Kranz DP, Velder J, Schmalz H.-G. Tetrahedron: Asymmetry 2011; 22: 887
- 13c Naeemi Q, Dindaroğlu M, Kranz DP, Velder J, Schmalz H.-G. Eur. J. Org. Chem. 2012; 1179
- 14 Lölsberg W, Ye S, Schmalz H.-G. Adv. Synth. Catal. 2010; 2023
- 15a Alexakis A, Bäckvall JE, Krause N, Pamies O, Dieguez M. Chem. Rev. 2008; 108: 2796
-
15b Harutyunyan SR, den Hartog T, Geurts K, Minnaard AJ, Feringa BL. Chem. Rev. 2008; 108: 2824
- 16a Robert T, Romanski S, Abiri Z, Wassenaar J, Reek JN. H, Schmalz H.-G. Organometallics 2010; 29: 478
- 16b Robert T, Abiri Z, Sandee AJ, Schmalz H.-G, Reek JN. H. Tetrahedron: Asymmetry 2010; 21: 2671
- 17 Falk A, Fiebig L, Neudörfl J.-M, Adler A, Schmalz H.-G. Adv. Synth. Catal. 2011; 353: 3357
- 18a Bohn MA, Schmidt A, Hilt G, Dindaroğlu M, Schmalz H.-G. Angew. Chem. Int. Ed. 2011; 50: 9689
- 18b Arndt M, Dindaroğlu M, Schmalz H.-G, Hilt G. Org. Lett. 2011; 13: 6236
- 18c Arndt M, Dindaroğlu M, Schmalz H.-G, Hilt G. Synthesis 2012; 44: 3534
- 18d For a recent review on hydrovinylation, see: Hilt G. Eur. J. Org. Chem. 2012; 4441
- 19 Fujisaki S, Eguchi H, Omura A, Okamoto A, Nishida A. Bull. Chem. Soc. Jpn. 1993; 66: 1576
- 20 Moulin D, Bago S, Bauduin C, Darcel C, Jugé S. Tetrahedron: Asymmetry 2000; 11: 3939
- 21 Acros ultra-pure silica gel for column chromatography, 40–60 μm, 60A.
For reviews, see:
For a review, see:
For reviews on enantioselective Cu-catalyzed transformations of Grignard reagents, see: