Modern Aldol Methods for the Total Synthesis of Polyketides

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Abstract

The aldol reaction is one of the most important methods for the stereoselective construction of polyketide natural products, not only for nature but also for synthetic chemistry. The tremendous development in the field of aldol additions during the last 30 years has led to more and more total syntheses of complicated natural products. This Review illustrates by means of selected syntheses of natural products the new variants of the aldol addition. This includes aldol additions with various metal enolates, as well as metal‐complex‐catalyzed, organocatalytic, and biocatalytic methods.

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Im Goldenen Zeitalter der Organokatalyse

Peter I. Dalko, Lionel Moisan (2004)

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The ying and yang of asymmetric aminocatalysis.

Benjamin List (2006)

During the last six years the asymmetric catalysis of carbonyl transformations via iminium ion and enamine intermediates using chiral amines as organocatalysts has grown most remarkably. In this personal account an overview of this area is given. The field can be divided into two sub areas: (a) Iminium catalysis, which is typically used for cycloadditions and conjugate additions to enals and enones and (b) Enamine catalysis, which is commonly used in electrophilic alpha-substitution reactions of ketones and aldehydes. A common origin of the two catalysis principles is proposed and their recent merger in tandem sequences is discussed.

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Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents.

B List (2004)

The chemistry of preformed enamines, especially their use as enolate equivalents, has been a well-investigated area of research since the early 1950s. However, enamine catalysis, the catalysis of carbonyl transformations via enamine intermediates by using primary and secondary amines as catalysts, has only been fully appreciated as a powerful strategy for asymmetric synthesis since the beginning of this century. Contributions from this laboratory to the revitalized interest in asymmetric enamine catalysis are summarized in this Account.