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Stereoselective Formation of Amines by Nucleophilic Addition to Azomethine Derivatives

Part of the Topics in Current Chemistry book series (TOPCURRCHEM,volume 343)

Abstract

This chapter describes state-of-the-art methods to prepare α-chiral amines by the addition of nonstabilized nucleophiles to imine derivatives. The first part of the chapter illustrates the most effective diastereoselective addition reaction (substrate controlled and chiral auxiliary based methods) whereas the second part focuses on catalytic asymmetric methods.

Keywords

  • Azomethine
  • Chiral amines
  • Chiral auxiliaries
  • Chiral catalysts
  • Chiral ligands
  • Nucleophilic addition

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Fig. 1
Scheme 1
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Fig. 3
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Scheme 2
Scheme 3
Scheme 4
Fig. 6
Fig. 7
Scheme 5
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Scheme 6
Fig. 9
Scheme 7
Fig. 10
Fig. 11
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18

Abbreviations

DuPHOS:

[2,5-Dimethylphospholano]benzene

EWG:

Electron-withdrawing group

PG:

Protecting group

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Charette, A.B., Lindsay, V. (2013). Stereoselective Formation of Amines by Nucleophilic Addition to Azomethine Derivatives. In: Li, W., Zhang, X. (eds) Stereoselective Formation of Amines. Topics in Current Chemistry, vol 343. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_492

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