Asymmetric 1,3-Dipolar Cycloadditions of Cyclic Stabilized Ylides Derived from Chiral 1,2-Amino Alcohols

Abstract

The use of structurally similar chiral non-racemic azomethine ylides, nitrones and azomethine imines derived from 1,2-aminol alcohols in asymmetric dipolar cycloadditions is reviewed. This general survey underlines the great synthetic potential of dipolar cycloadditions, especially in a diversity-oriented approach and enables a direct comparison of the reactivity of apparently closely related reactive systems.

1 Introduction

2 Azomethine Ylides

2.1 Reactions Involving Ylides Derived from Formaldehyde

2.2 Reactions Involving Ylides Derived from Aliphatic or Aromatic Aldehydes

2.3 Reactions Involving Ylides Derived from Alkyl Glyoxylates or Ketones

2.4 Synthetic Applications

3 Nitrones

3.1 Reactions with Alkenes

3.2 Synthetic Applications

4 Azomethine Imines

4.1 Ylide Generation

4.2 Reactions Involving Ylides Derived from Aliphatic or Aromatic Aldehydes

4.3 Reactions Involving Ylides Derived from Alkyl Glyoxylates

4.4 Synthetic Applications

5 Conclusion

Key words

cycloadditions - ylides - stereoselective synthesis - heterocycles - multicomponent reactions

References and Notes

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24

The same side reaction has been observed by Harwood and co-workers, see ref. 19.

31

Despite a longer synthetic pathway, the hydroxylamine route delivers the nitrone as a crystalline material, whereas the product coming from the direct oxidation of the morpholinone has been described as an orange oil, see ref. 28 and 29.

38

CAUTION: Nitrosoamines are known to be highly toxic and must be handled with care.

45

The lower yield could be explained by the degradation of the dipolarophile during the slow cycloreversion process.