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. 2009 Feb 11;131(5):1674-5.
doi: 10.1021/ja809181m.

Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes

Barry M Trost  1 , Sushant Malhotra, Benjamin A Fried
Affiliations

Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes

Barry M Trost et al. J Am Chem Soc. .

Abstract

Magnesium-catalyzed enantioselective aldol between ethyl diazoacetate and aromatic, aliphatic, and alpha,beta-unsaturated aldehydes affords alpha-diazo-beta-hydroxy-esters in high enantioselectivities. Aldol adducts resulting from this asymmetric transformation are versatile intermediates toward the synthesis of several ester containing chiral building blocks.

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Figures

Figure 1
Figure 1
Bu2Mg-ProPhenol 1-catalyzed aldol reaction.
Figure 2
Figure 2
Conditions: (a) Et3B, THF, rt; (b) DMDO, CH2Cl2, −35 ºC; then NaBH4, CH2Cl2, −78 ºC; (c) (i) TBDMSCl, Imidazole, CH2Cl2; (ii) Pd(C), H2, EtOAc.
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References

    1. Notz W, Tanaka F, Barbas CF., III Acc Chem Res. 2004;37:580. - PubMed
    2. Northrup AB, MacMillan DWC. J Am Chem Soc. 2002;124:6798. - PubMed
    1. Trost BM, Ito H. J Am Chem Soc. 2000;122:12033.
    2. Trost BM, Ito H, Silcoff ER. J Am Chem Soc. 2001;123:3367. - PubMed
    3. Suzuki T, Yamagiwa N, Matsuo Y, Sakamoto S, Yamaguchi K, Shibsaki M, Noyori R. Tetrahedron Lett. 2001;42:4669.
    4. Gnanadesikan V, Horiuchi Y, Ohshima T, Shibasaki M. J Am Chem Soc. 2004;126:7782. and references therein. - PubMed
    5. Li H, Da CS, Xiao YH, Li X, Su YN. J Org Chem. 2008;73:7398. - PubMed
    1. Denmark SE, Stavenger RA. Acc Chem Res. 2000;33:432. and references therein. - PubMed
    2. Carreira EM, Singer RA, Lee W. J Am Chem Soc. 1994;116:8837.
    3. Mikami K, Matsukawa S. J Am Chem Soc. 1994;116:4077.
    1. Yao W, Wang J. Org Lett. 2003;5:1527. - PubMed
    2. Hasegawa K, Arai S, Nishida A. Tetrahedron. 2006;62:1390.
    3. Suto Y, Tsuji R, Kanai M, Shibasaki M. Org Lett. 2005;7:3757. - PubMed
    4. Li L, Klauber EG, Seidel D. J Am Chem Soc. 2008;130:12248. - PubMed
    5. Magdziak D, Lalic G, Lee HM, Fortner KC, Aloise AD, Shair MD. J Am Chem Soc. 2005;127:7284. - PubMed
    6. Evans DA, Downey CW, Hubbs JL. J Am Chem Soc. 2003;125:8706. - PubMed
    7. Ooi T, Kameda M, Taniguchi M, Maruoka K. J Am Chem Soc. 2004;126:9685. - PubMed
    8. Saito S, Kobayashi S. J Am Chem Soc. 2006;128:8704. - PubMed
    1. Kumagai N, Matsunaga S, Kinoshita T, Harada S, Okada S, Sakamoto S, Yamaguchi K, Shibasaki M. J Am Chem Soc. 2003;125:2169. - PubMed

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