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. 2007 Jun 13;129(23):7274-6.
doi: 10.1021/ja071905g. Epub 2007 May 22.

syn-1,2-Amino alcohols via diastereoselective allylic C-H amination

Kenneth J Fraunhoffer  1 , M Christina White
Affiliations

syn-1,2-Amino alcohols via diastereoselective allylic C-H amination

Kenneth J Fraunhoffer et al. J Am Chem Soc. .
No abstract available

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Figures

Scheme 1<sup>a</sup>
Scheme 1a
a Conditions: (a) RuCl3 (5 mol %), NaIO4 (5 equiv), CH3CN/CCl4/H2O (2:2:3), room temp (82%); (b) sodium naphthalene (8 equiv), DME, −78 °C; (c) 6 M HCl, 100 °C (63%, two steps).
Scheme 2<sup>a</sup>
Scheme 2a
a Conditions: (a) 1 (10 mol %), 5 mol % additional bis-sulfoxide, PhBQ (1.05 equiv), THF (0.66 M), 45 °C, 72 h; (b) BCl3 (5 equiv), CH2Cl2, room temp, 72%.
Scheme 3
Scheme 3
Scheme 4
Scheme 4
See this image and copyright information in PMC

References

    1. C–O to C–N catalyzed by Pd(0): Trost BM, Sudhakar AR. J Am Chem Soc. 1987;109:3792.Trost BM, Patterson DE. J Org Chem. 1998;63:1339.Hayashi T, Yamamoto A, Ito Y. Tetrahedron Lett. 1988;29:99.Bystrom SE, Aslanian R, Backvall JE. Tetrahedron Lett. 1985;26:1749.Hayashi T, Kishi K, Yamamoto A, Ito Y. Tetrahedron Lett. 1990;31:1743.Evans PA, Robinson JE, Nelson JD. J Am Chem Soc. 1999;121:6761.Ohmura T, Hartwig JF. J Am Chem Soc. 2002;124:15164.Olefin aminohydroxylation: Kolb HC, Sharpless KB. In: Transition Metals for Organic Synthesis. 2. Beller M, Bolm C, editors. Wiley-VCH Verlag; Weinheim, Germany: 2004. p. 309.Mannich: Trost BM, Terrell LR. J Am Chem Soc. 2003;125:338.Matsunaga S, Yoshida T, Morimoto H, Kumagai N, Shibasaki M. J Am Chem Soc. 2004;126:8777.Ramasastry SSV, Zhang H, Tanaka F, Barbas CF. J Am Chem Soc. 2007;129:288.

    1. Streamlining syntheses via late stage C–H oxidation see: Fraunhoffer KJ, Bachovchin DA, White MC. Org Lett. 2005;7:223.Covell DJ, Vermeulen NA, Labenz NA, White MC. Angew Chem, Int Ed. 2006;45:8217.Hoffman RW. Synthesis. 2006;21:3531.Elegant examples of late stage C–H hydroxylation and amination see: Wender PA, Hilinski MK, Mayweg AVW. Org Lett. 2005;7:79.Hinman A, Du Bois J. J Am Chem Soc. 2003;125:11510.

    1. C-H amination via metal nitrenes: Espino CG, Du Bois J. Angew Chem, Int Ed. 2001;40:598.Kim M, Mulcahy JV, Espino CG, Du Bois J. Org Lett. 2006;8:1073.Lebel H, Huard K, Lectard S. J Am Chem Soc. 2005;127:14198.

    1. For single examples of catalytic allylic C–H amination: (a) ref 3b. Larock RC, Hightower TR, Hasvold LA, Peterson KP. J Org Chem. 1996;61:3584.

    1. Hegedus LS, Allen GF, Waterman EL. J Am Chem Soc. 1976;98:2674.Ronn M, Backvall JE, Andersson PG. Tetrahedron Lett. 1995;36:7749. (c) ref. 4b. Overman LE, Remarchuk TP. J Am Chem Soc. 2002;124:12.Brice JL, Harang JE, Timokhin VI, Anastasi NR, Stahl SS. J Am Chem Soc. 2005;127:2868.

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