- Reformatsky reaction
The Reformatsky reaction (sometimes spelled Reformatskii reaction) is an
organic reaction which condensesaldehyde s 1 (orketone s) with α-haloester s 2 with metalliczinc to form β-hydroxy-esters 3.Ref|ReformatskyRef|Reformatsky2 It was discovered bySergei 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.Ref|ShrinerRef|Rathke
Variations
In one variation of the Reformatsky reactionRef|Lambert an iodolactone is coupled with an
aldehyde withtriethylborane intoluene at -78°C.ee also
* Example use in total synthesis:
Mukaiyama Taxol total synthesis (B ring construction)References
# Reformatskii, S., Neue Synthese zweiatomiger einbasischer Säuren aus den Ketonen, "
Ber. " 1887, "20", 1210. doi|10.1002/cber.188702001268
# 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. DanishefskyJ. Am. Chem. Soc. 2006, 128(2), 426 - 427. (Communication) doi|10.1021/ja0574567 S0002-7863(05)07456-1 [http://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/ja0574567 Abstract]ee also
*
Aldol reaction
*Blaise reaction
*Claisen condensation
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