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DOI: 10.1055/s-0028-1083451
Copper-Catalyzed Cycloaddition of Bis-Sulfonyl Ethylene
Contributor(s):Hisashi Yamamoto, Marina NaodovicUniversidad Autónoma de Madrid, Spain
Bis-Sulfonyl Ethylene as Masked Acetylene Equivalent in Catalytic Asymmetric [3+2] Cycloaddition of Azomethine Ylides
J. Am. Chem. Soc. 2008, 130: 10084-10085
Publication History
Publication Date:
23 October 2008 (online)
Key words
copper - azomethine ylides - cycloaddition
Significance
Asymmetric [3+2] cycloadditions of azomethine ylides are one the most efficient protocols for the preparation of chiral pyrrolidines. The major drawback of these reactions is the limitation in substrate scope of electron-deficient dipolarophiles. In this report, Carretero and co-workers introduce bis-sulfonyl ethylene which acts as an acetylene surrogate, species which are unprecedented substrates for cycloaddition with azomethine ylides.
Comment
This account represents a great contribution to the area of azomethine ylide cycloaddition reactions. Advantages of the methodology are numerous. Starting form commercially available substrates, under mild conditions and short reaction times, highly complex chiral pyrrolidines are formed in good yields and high enantioselectivities. The authors have also demonstrated that the products can be further elaborated and showcased it with the short synthesis of Schramm’s C-azanucleoside.