Synlett 2012; 23(6): 953-954
DOI: 10.1055/s-0031-1290774
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© Georg Thieme Verlag Stuttgart · New York

(S)-α,α-Diphenylprolinol Trimethylsilyl Ether

Aneta Wróblewska
Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland, Email: anetka.wroblewska@gmail.com
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Further Information

Publication History

Publication Date:
16 March 2012 (eFirst)

Introduction

One of the most important sections of modern organic chemistry is asymmetric synthesis, and in this field particularly attractive are problems relating to asymmetric catalysis. In the recent two decades, special attention is focused on (S)-proline and its derivatives, which are known as versatile organocatalysts (‘aminocatalysts’).[1] [2] It was found that the introduction of the protecting silyl moiety into the prolinol structure results in a remarkable increase of catalytic activity, thus allowing decrease in catalyst loading and shorter reaction times without compromising the level of enantioselectivity.[ 3 ] In addition, this modification leads to significant broadening of the substrate scope. First examples of applications of the O-silyl prolinol derivatives in asymmetric synthesis were independently reported by Hayashi[ 3 ] and Jørgensen.[ 4 ] Since then these compounds have been used efficiently as ‘privileged catalysts’[ 2b ] in diverse organic transformations, such as epoxidations, aldol, anti-selective Mannich, ­Friedel–Crafts and Diels–Alder reactions, etc.[5] [6] Probably, the most prominent representative of diarylprolinol derivatives containing the silyl moiety is (S)-α,α-diphenyl­prolinol trimethylsilyl ether (1).

 
  • References

  • 1 List B. Tetrahedron 2002; 58: 5573
    • 2a Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138
    • 2b Zhang S, Wang W. Proline Derivatives. In Privileged Chiral Ligands and Catalysts. Zhou Q.-L. Wiley-VCH Verlag; Weinheim: 2011. Chap. 11, 40
  • 3 Hayashi Y, Gotoh H, Hayashi T, Shoji M. Angew. Chem. Int. Ed. 2005; 44: 4212; Angew. Chem. 2005, 117, 4284
  • 4 Marigo M, Wabnitz TC, Fielenbach D, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 794 ; Angew. Chem. 2005, 117, 804
  • 5 Palomo C, Mielgo A. Angew. Chem. Int. Ed. 2006; 45: 7876
  • 6 Xu L.-W, Li L, Shi Z.-H. Adv. Synth. Catal. 2010; 352: 243
  • 7 Xu F, Zacuto M, Yoshikawa N, Desmond R, Hoerrner S, Itoh T, Journet M, Humphrey GR, Cowden C, Strotman N, Devine P. J. Org. Chem. 2010; 75: 7829
    • 8a Boeckman Jr RK, Miller JR. Org. Lett. 2009; 11: 4544
    • 8b Mielgo A, Velilla I, Gomez-Bengoa E, Palomo C. Chem. Eur. J. 2010; 16: 7496
    • 9a Hayashi Y, Itoh T, Ohkubo M, Ishikawa H. Angew. Chem. Int. Ed. 2008; 47: 4722 ; Angew. Chem. 2008 120 4800
    • 9b Patora-Komisarska K, Benoboud M, Ishikawa H, Seebach D, Hayashi Y. Helv. Chim. Acta 2011; 94: 719
    • 10a Ibrahem I, Córdova A. Chem. Commun. 2006; 1760
    • 10b Fustero S, Mojarrad F, Perez Carrion MD, Sanz-Carvera JF, Acena JL. Eur. J. Org. Chem. 2009; 5208
  • 11 Zhao G.-L, Ibrahem I, Sundén H, Córdova A. Adv. Synth. Catal. 2007; 349: 1210
  • 12 Jia Z.-J, Jiang H, Li J.-L, Gschwend B, Li Q.-Z, Yin X, Grouleff J, Chen Y.-C, Jørgensen KA. J. Am. Chem. Soc. 2011; 133: 5053
  • 13 Hong L, Wang L, Chen C, Zhang B, Wang R. Adv. Synth. Catal. 2009; 351: 772