Stereoselective Synthesis of Indanylglycine Derivatives by a Tandem Michael–Michael Reaction

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.

Key words

amino acids - carbanions - carbocycles - Michael addition - tandem reaction

• References and Notes


For review articles, see:
• 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

For recent reports on tandem Michael–Michael reactions, see for example:
• 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