Reformatskii reaction
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The Reformatskii 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.
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.
[edit] Variations
In one variation of the Reformatsky reaction an iodolactone is coupled with an aldehyde with triethylborane in toluene at -78°C.
[edit] References
- ^ Reformatskii, S. Ber. 1887, 20, 1210.
- ^ Reformatskii, S. J. Russ. Phys. Chem. Soc. 1890, 22, 44.
- ^ Shriner, R. L. Org. React. 1942, 1, 1. (Review)
- ^ Rathke, M. W. Org. React. 1975, 22, 423. (Review)
- ^ Total Synthesis of UCS1025A Tristan H. Lambert and Samuel J. Danishefsky J. Am. Chem. Soc. 2006, 128(2), 426 - 427. (Communication) DOI: 10.1021/ja0574567 Abstract
