SnAP Reagent

SnAP Reagent

Overall Score4
  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • Contribution to Medicinal Chemistry
  • General Characteristics

SnAP (Sn(tin) Amine Protocol) reagents provide an easy access to a variety of saturated heterocycles and amines containing a spiro skeleton. The simple two-step procedure involves initial imine formation and oxidative cyclization. The reagents are stable and can be handled easily, and many types are commercially available.

Increasing the saturation of heterocycles (proportion of sp3 carbons) in pharmaceutical compounds is expected to have beneficial physicochemical effects.

  • General References

Vo, C.-V.; Mikutis, G.; Bode, J. W. Angew. Chem. Int. Ed. 2013, 52, 1705. DOI: 10.1002/anie.201208064

Luescher, M. U.; Vo, C.-V.; Bode, J. W. Org. Lett. 2014, 16, 1236. DOI: 10.1021/ol500210z

Vo, C.-V.; Luescher, M. U.; Bode, J. W. Nat. Chem. 2014, 6, 310. doi:10.1038/nchem.1878

Siau, W.-Y.; Bode, J. W. J. Am. Chem. Soc. 2014, 136, 17726. DOI: 10.1021/ja511232b

Geoghegan, K.; Bode, J. W. Org. Lett. 2015, 17, 1934. DOI: 10.1021/acs.orglett.5b00618

Luescher, M. U.; Bode, J. W. Angew. Chem. Int. Ed. 2015, 54, 10884. DOI: 10.1002/anie.201505167

Luescher, M. U.; Bode, J. W. Org. Lett. 2016, 18, 2652. DOI: 10.1021/acs.orglett.6b01099


Vo, C.-V.; Bode, J. W. J. Org. Chem. 2014, 79, 2809. DOI: 10.1021/jo5001252

Luescher, M. U.; Geoghegan, K.; Nichols, P. L.; Bode, J. W. Aldrichim. Acta 2015, 48, 43. [PDF]

  • Reaction Mechanism

  • Examples

When used for ketone substrates, spiro-products can be synthesized, which are challenging to access otherwise.

Tin-free and photo-activated SLAP (Silicon Amine Protocol) reagents have been reported.[1]

  • Experimental Procedure

  • Experimental Tips

  • References

[1] (a) Hsieh, S.-Y.; Bode, J. W. Org. Lett. 2016, 18, 2098. DOI: 10.1021/acs.orglett.6b00722 (b) Hsieh, S-H.; Bode, J. W. ACS Cent. Sci. 2017, 3, 66. DOI: 10.1021/acscentsci.6b00334

  • Related Reactions

  • Related Books

  • External Links

Bode Research Group

Bode Group – Professor Product Portal (Sigma-Aldrcih)


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