Ketene Dithioacetals in Organic Synthesis: Recent Developments
- 1 January 1990
- journal article
- review article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (03) , 171-190
- https://doi.org/10.1055/s-1990-26824
Abstract
Ketene dithioacetals are reviewed as versatile building blocks in a multitude of synthetically useful transformations. After discussing the methods for preparation of ketene dithioacetals, their application in cyclizations, C-C bond formation and in the synthesis of heterocyclic systems will be described. Their use as carboxyl equivalents, which display an umpolung-type reactivity pattern will be emphasized. 1 Introduction 2.Synthesis of Ketene Dithioacetals 2.1. Synthesis of Nonfunctionalized Ketene Dithioacetals 2.1.1. From Aldehydes and Ketones by Olefination 2.1.2. From Esters or Ester Equivalents 2.1.3. From Dithioacetals 2.1.4 From 1,1-Dihetero Substituted Olefins 2.2. Synthesis of Polyfunctional Ketene Dithioacetats 3. Ketene Dithioacetals in Organic Synthesis 3.1. a1,d2,a3... : Normal Reactivity 3.2. d1, a2, d3...: Umpolung-Type Reactivity 3.3. Polyfunctional Ketene Dithioacetals in Organic Synthesis 3.3.1.α-Oxo Ketene Dithioacetals 3.3.2. Nitro Ketene Dithioacetals 3.3.3. Miscellaneous 4. ConclusionKeywords
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