Journal
RUSSIAN CHEMICAL BULLETIN
Volume 70, Issue 7, Pages 1213-1259Publisher
SPRINGER
DOI: 10.1007/s11172-021-3208-1
Keywords
[3; 3]-sigmatropic rearrangements; Fischer; Claisen; and Cope reactions; ketenes; allenes; oxygen-; nitrogen-; and sulfur-containing heterocycles; alkaloids
Categories
Funding
- Russian Foundation for Basic Research [19-13-50451]
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This review summarizes the synthesis of heterocyclic compounds using [3,3]-sigmatropic transformations, covering reactions such as the Fischer, Claisen, and Cope rearrangements. These methods are shown to be efficient for synthesizing complex heterocyclic systems with multiple chiral centers, and can be used in the construction of medium size heterocycles containing oxygen, nitrogen, and sulfur, as well as in the synthesis of condensed systems and natural compounds.
The review summarizes the data on the synthesis of heterocyclic compounds by means of [3,3]-sigmatropic transformations, which include the Fischer, Claisen, and Cope rearrangements, as well as their numerous variations. These reactions have proved to be a convenient and efficient method for the synthesis of complex and poorly available heterocyclic systems with several chiral centers due to the highly ordered transition state of the process. Methods for the construction of five- and six-membered and medium size oxygen-, nitrogen-, and sulfur- containing heterocycles are described, as well as their use in the synthesis of condensed systems and natural compounds.
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