Reformatsky reaction

Reformatsky reaction

The Reformatsky reaction (sometimes spelled 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.Ref|ReformatskyRef|Reformatsky2 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.Ref|ShrinerRef|Rathke

Variations

In one variation of the Reformatsky reactionRef|Lambert an iodolactone is coupled with an aldehyde with triethylborane in toluene 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. Danishefsky J. 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


Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • Réaction de Reformatsky — La réaction de Reformatsky (parfois notée Reformatskii) est une réaction de chimie organique qui consiste en une condensation entre un aldéhyde (ou une cétone) 1 et un ester alpha halogéné 2, avec l aide d un catalyseur au zinc métallique. Le… …   Wikipédia en Français

  • Reacción de Reformatsky — Saltar a navegación, búsqueda La reacción de Reformatsky (algunas veces escrito reacción de Reformatskii) es una síntesis orgánica que condensa aldehídos 1 o cetonas con ésteres 2 de α halo con zinc metalico para formar ésteres de nomenclatura… …   Wikipedia Español

  • Aldol reaction — The aldol reaction is a powerful means of forming carbon–carbon bonds in organic chemistry.[1][2][3] Discovered independently by …   Wikipedia

  • Blaise reaction — The Blaise reaction is an organic reaction that forms a β ketoester from the reaction of zinc metal with a α bromoester and a nitrile.Ref|Blaise1901 Ref|OS1955 Ref|Rao2008 The final intermediate is a metaloimine, which is hydrolyzed to give the… …   Wikipedia

  • Sergey Reformatsky — Infobox Scientist name = Sergey Nikolaevich Reformatsky caption = birth date = April 1, 1860 birth place = Borisoglebskoe, near Ivanovo, Russia residence = Russia, Germany nationality = russian death date = death date and… …   Wikipedia

  • List of Russian chemists — A sculpture in honor of Dmitry Mendeleev and his Periodic table in Slovakia. This list of Russian chemists includes the famous chemists and material scientists of the Russian Federation, the Soviet Union, the Russian Empire and other predecessor… …   Wikipedia

  • List of Russian people — The Millennium of Russia monument in Veliky Novgorod, featuring the statues and reliefs of the most celebrated people in the first 1000 years of Russian history …   Wikipedia

  • Liste De Réactions Chimiques — Liste des réactions chimiques par ordre alphabétique. Sommaire : Haut A B C D E F G H I J K L M N O P Q R S T U V W X Y Z A Acétal …   Wikipédia en Français

  • Liste de reactions chimiques — Liste de réactions chimiques Liste des réactions chimiques par ordre alphabétique. Sommaire : Haut A B C D E F G H I J K L M N O P Q R S T U V W X Y Z A Acétal …   Wikipédia en Français

  • Liste de réactions chimiques — Liste des réactions chimiques par ordre alphabétique. Sommaire : Haut A B C D E F G H I J K L M N O P Q R S T U V W X Y Z A Acétalisation …   Wikipédia en Français

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”