Facile, regio and stereoselective Diels-Alder reactions of allenic trichloromethyl sulfones and sulfoxides

Samuel Braverman; Zvi Lior

doi:10.1016/s0040-4039(00)73478-2

Facile, regio and stereoselective Diels-Alder reactions of allenic trichloromethyl sulfones and sulfoxides

Samuel Braverman, Zvi Lior

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

The dienophilic reactivity of allenes is drastically increased by the powerful electron withdrawing trichloromethylsulfonyl or sulfinyl substituents. The [4+2]-cycloadditions proceed smoothly with high regio- and stereoselectivity under mild conditions. Using an optically active allenyl sulfone, transfer of chirality has been observed.

Original language	English
Pages (from-to)	6725-6728
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	36
DOIs	https://doi.org/10.1016/s0040-4039(00)73478-2
State	Published - 5 Sep 1994

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title = "Facile, regio and stereoselective Diels-Alder reactions of allenic trichloromethyl sulfones and sulfoxides",

abstract = "The dienophilic reactivity of allenes is drastically increased by the powerful electron withdrawing trichloromethylsulfonyl or sulfinyl substituents. The [4+2]-cycloadditions proceed smoothly with high regio- and stereoselectivity under mild conditions. Using an optically active allenyl sulfone, transfer of chirality has been observed.",

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N2 - The dienophilic reactivity of allenes is drastically increased by the powerful electron withdrawing trichloromethylsulfonyl or sulfinyl substituents. The [4+2]-cycloadditions proceed smoothly with high regio- and stereoselectivity under mild conditions. Using an optically active allenyl sulfone, transfer of chirality has been observed.

AB - The dienophilic reactivity of allenes is drastically increased by the powerful electron withdrawing trichloromethylsulfonyl or sulfinyl substituents. The [4+2]-cycloadditions proceed smoothly with high regio- and stereoselectivity under mild conditions. Using an optically active allenyl sulfone, transfer of chirality has been observed.

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Facile, regio and stereoselective Diels-Alder reactions of allenic trichloromethyl sulfones and sulfoxides

Abstract

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