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

Recognize and detect the effects of electrostatic charges on your balance

How to quickly check pipettes?

Don't let static charges disrupt your weighing accuracy

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