Mukaiyama Aldol Reactions in Aqueous Media

  • Author: Veronika Belusa
  • Published: 05 November 2013
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Advanced Synthesis & Catalysis (ASC)/Wiley
thumbnail image: Mukaiyama Aldol Reactions in Aqueous Media

The development of one of the most reliable C-C bond-forming reactions in organic synthesis, the Mukaiyama aldol reaction, is surveyed by Taku Kitanosono and Shu Kobayashi, University of Tokyo, Japan.
The original Mukaiyama aldol reactions were carried out with a silyl enol ether and an aldehyde using stoichiometric amounts of Lewis acids such as TiCl4 in organic solvents under strictly anhydrous conditions (pictured). Efforts to develop the reaction in aqueous media led to many fruitful scientific advances not only in organic chemistry and organic synthesis but also in inorganic chemistry and biochemistry.


For example, in 1991 it was found that Mukaiyama aldol reactions proceeded under milder conditions and obtained high yields with wide substrate scope in the presence of a catalytic amount of lanthanide triflates in aqueous solvents. This finding put aside the former believes that Lewis acids decompose rapidly even in the presence of small amounts of water. This lead to the discovery of a series of water-compatible Lewis acids.


The chemistry in this field is still being actively pursued. Compared with the well-refined catalytic systems for asymmetric hydroxymethylation in aqueous media, contemporary catalysts for reactions between hydrophobic substrates have the fault of substrate specificity and lack broader catalytic activities.


This review is published in celebration of the 40th anniversary of the Mukaiyama Reaction.

Article Views: 3360

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH