RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2012; 23(18): 2653-2656
DOI: 10.1055/s-0032-1317447
DOI: 10.1055/s-0032-1317447
letter
Stereoselective Synthesis of Indanylglycine Derivatives by a Tandem Michael–Michael Reaction
Weitere Informationen
Publikationsverlauf
Received: 11. September 2012
Accepted after revision: 21. September 2012
Publikationsdatum:
18. Oktober 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201218/lookinside/thumbnails/10.1055-s-0032-1317447-1.jpg)
Abstract
The construction of 1,2,3-trisubstituted indane rings by the Michael addition of a glycinate followed by an intramolecular Michael cyclization is reported. The tandem process affords indanylglycine derivatives with high regio- and diastereoselectivity.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1a Guo H.-C, Ma J.-A. Angew. Chem. Int. Ed. 2006; 45: 354
- 1b Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
- 1c Alba A.-N, Compayó X, Viciano M, Rios R. Curr. Org. Chem. 2009; 13: 1432
- 2a Navarro C, Csákÿ AG. Org. Lett. 2008; 10: 217
- 2b Landa A, Puente A, Santos JA, Vera S, Oiarbide M, Palomo C. Chem.–Eur. J. 2009; 15: 11954
- 2c Navarro C, Csákÿ AG. Synthesis 2009; 860
- 2d Sánchez-Larios E, Gravel M. J. Org. Chem. 2009; 74: 7536
- 2e Yazaki R, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 10275
- 2f Kirchberg S, Fröhlich R, Studer A. Angew. Chem. Int. Ed. 2010; 49: 6877
- 2g Biswas A, Sarkar SD, Fröhlich R, Studer A. Org. Lett. 2011; 13: 4966
- 3 See: Merino P. Science of Synthesis . Vol. 45a. Siegel JS. Thieme; Stuttgart: 2009: 253 ; and references cited therein
- 4a Li H, Zu LS, Xie HX, Wang J, Jiang W, Wang W. Org. Lett. 2007; 9: 1833
- 4b Silvanus AC, Groombridge BJ, Andrews BI, Kociok-Köhn G, Carbery DR. J. Org. Chem. 2010; 75: 7491
- 4c Ma AQ, Ma DW. Org. Lett. 2010; 12: 3634
- 4d Wu B, Liu G.-G, Li M.-Q, Zhang Y, Zhang S.-Y, Qiu J.-R, Xu X.-P, Ji S.-J, Wang X.-W. Chem. Commun. 2011; 47: 3992
- 4e Hong B.-C, Nimje RY, Lin C.-W, Liao J.-H. Org. Lett. 2011; 13: 1278
- 4f Li X.-M, Wang B, Zhang J.-M, Yan M. Org. Lett. 2011; 13: 374
- 5 Michaux J, Niel G, Campagne J.-M. Chem. Soc. Rev. 2009; 38: 2093
- 6 Ashton WT, Dong H, Xu J. WO 2005044195, 2005
- 7 Curry K. WO 2001002340, 2001
- 8 Kondo T, Itahana H, Tobe T, Togami J, Tsukamoto S. JP 09157253, 1997
- 9 Stewart JM, Gera L, Whalley ET. WO 9616081, 1996
- 10 Burke TR. Jr, Barchi JJ, George C, Wolf G, Shoelson SE, Yan X. J. Med. Chem. 1995; 38: 1386
- 11 Josien H, Lavielle S, Brunissen A, Saffroy M, Torrens Y, Beaujouan J.-C, Glowinski J, Chassaing G. J. Med. Chem. 1994; 37: 1586
- 12 Kotha S, Krishna NG, Misra S, Khedkar P. Synthesis 2011; 2945
- 13 See Supporting Information.
- 14 Representative Procedure BuLi (1.6 M solution in hexanes, 1.25 equiv, 227 μL, 0.36 mmol) was added to a solution of i-Pr2NH (45 μL, 1.1 equiv, 0.32 mmol) in THF (0.3 mL) at –78 °C. After 30 min, a solution of 2b (0.29 mmol) in THF (0.3 mL) was added, and the mixture stirred for 30 min. A solution of 1 (0.29 mmol) in THF (0.3 mL) was added, the temperature allowed to raise slowly from –78ºC to r.t., and the mixture stirred for 24 h. After addition of H2O (5 mL), the organic layer was separated, and the aqueous layer extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was washed with H2O, dried over MgSO4, filtered, and evaporated under reduced pressure. The product was purified by chromatography on silica gel (hexane–EtOAc = 70:30).
- 15 Determined by the correlations found in the HMQC and HMBC spectra. See Supporting Information.
- 16 Alvarez-Ibarra C, Csákÿ AG, Maroto M, Quiroga ML. J. Org. Chem. 1995; 60: 6700
For review articles, see:
For recent reports on tandem Michael–Michael reactions, see for example: