Synthetic Applications of the Retro-Ene Reaction

Jean-Louis Ripoll; Yannick Vallée

doi:10.1055/s-1993-25918

Synthesis 1993; 1993(7): 659-677
DOI: 10.1055/s-1993-25918

review

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Synthetic Applications of the Retro-Ene Reaction

Jean-Louis Ripoll^* , Yannick Vallée

^*Laboratoire des Composés Thio-organiques, URA CNRS 480, ISMRA, Université de Caen, F-14050 Caen, France

Abstract

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During the past two decades, a number of synthetic works have used the retro-ene reaction, showing clearly the broad scope and the advantages of this thermal monomolecular cleavage for the stereo-specific obtention of unsaturated and often reactive species. The present review brings together a selection of the relevant literature between 1970 and 1991 (partly 1992). 1. Introduction 2. All-Carbon Retro-Ene Reactions 3. Oxygen Hetero-Retro-Ene Reactions 3.1. 1-O Ene Adducts 3.2. 2-O Ene Adducts 3.3. 3-O Ene Adducts 3.4. 1-O, 3-O; 1-O, 5-O and 2-O, 5-O Ene Adducts 4. Nitrogen Hetero-Retro-Ene Reactions 4.1. 1-N Ene Adducts 4.2. 2-N Ene Adducts 4.3. 4-N and 5-N Ene Adducts 4.4. 1-N, 2-N Ene Adducts 4.5. 1-O, 5-N and 3-O, 5-N Ene Adducts 4.6. 1-N, 3-N, 5-O; 2-O, 3-N, 5-N and 1-O, 2-O, 4-N, 5-N Ene Adducts 5. Sulfur Hetero-Retro-Ene Reactions 5.1. 2-S Ene Adducts 5.2. 1-O, 2-S Ene Adducts 5.3. 1-O, 5-S and 2-S, 5-O Ene Adducts 5.4. 1-N, 2-S Ene Adducts 6. Silicon (and Germanium) Hetero-Retro-Ene Reactions 6.1. 2-Si (and 2-Ge) Ene Adducts 6.2. 5-Si Ene Adducts 6.3. 1-Si, 2-O and 1-Si, 2-N Ene Adducts 6.4. 2-Si, 3-O Ene Adducts 7. Internal Retro-Ene Reactions 7.1. All-C Bridged Ene Adducts 7.1.1. 1,5-Bridged Ene Adducts 7.1.2. 2,3-Bridged Ene Adducts 7.2. Bridged Hetero Ene Adducts 7.2.1. 2,3-Bridged 1-O Ene Adducts 7.2.2. 2,3-Bridged 5-O Ene Adducts 7.2.3. 2,3-Bridged 1-N, 5-O and 3-N, 5-N Ene Adducts 8. Conclusion

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