Reformatskii reaction

The Reformatskii reaction (often spelled Reformatsky reaction) is an organic reaction which condenses aldehydes 1 (or ketones) with α-halo esters 2 with metallic zinc to form β-hydroxy-esters 3.^[1][2] It was discovered by Sergei Nikolaevich Reformatskii.

The organozinc reagent, also called a 'Reformatskii enolate', is prepared by treating an alpha-halo ester with zinc dust. Reformatskii enolates are less reactive than Grignard reagents and hence nucleophillic addition to the ester group does not occur.

Some reviews have been published.^[3][4]

Additional recommended knowledge

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Variations

In one variation of the Reformatsky reaction^[5] an iodolactone is coupled with an aldehyde with triethylborane in toluene at -78°C.

See also

• Example use in total synthesis: Mukaiyama Taxol total synthesis (B ring construction)

References

1. ^  Reformatskii, S., Neue Synthese zweiatomiger einbasischer Säuren aus den Ketonen, Ber. 1887, 20, 1210. doi:10.1002/cber.188702001268
2. ^  Reformatskii, S. J. Russ. Phys. Chem. Soc. 1890, 22, 44.
3. ^  Shriner, R. L. Org. React. 1942, 1, 1. (Review)
4. ^  Rathke, M. W. Org. React. 1975, 22, 423. (Review)
5. ^  Total Synthesis of UCS1025A Tristan H. Lambert and Samuel J. Danishefsky J. Am. Chem. Soc. 2006, 128(2), 426 - 427. (Communication) doi:S0002-7863(05)07456-1 10.1021/ja0574567 S0002-7863(05)07456-1 Abstract

See also

• Aldol reaction
• Blaise reaction
• Claisen condensation