Abstract
Sulfonate and sulfonamide are electron withdrawing activators for both vinyl and acetylenic units. These vinyl (acyclic and cyclic) and acetylenic sulfonates and sulfonamides are versatile dienophiles in inter- and intramolecular Diels-Alder reactions, as well as dipolarophiles in 1,3-dipolar cycloadditions. Asymmetric versions of these cycloaddition reactions are also known. Further manipulation of the cycloaddition products afforded interesting compounds that are useful synthons and building blocks in natural product synthesis and asymmetric synthesis.
Keywords: Sulfonate, Sulfonamide, Olefins, dipolarophiles, Diels-Alder reactions
Current Organic Chemistry
Title: Sulfonate and Sulfonamide Activated Olefins and Acetylenes in [4+2] Cycloaddition Reactions
Volume: 7 Issue: 6
Author(s): Albert W.M. Lee, W. H. Chan, H. K. Zhang and P. F. Xia
Affiliation:
Keywords: Sulfonate, Sulfonamide, Olefins, dipolarophiles, Diels-Alder reactions
Abstract: Sulfonate and sulfonamide are electron withdrawing activators for both vinyl and acetylenic units. These vinyl (acyclic and cyclic) and acetylenic sulfonates and sulfonamides are versatile dienophiles in inter- and intramolecular Diels-Alder reactions, as well as dipolarophiles in 1,3-dipolar cycloadditions. Asymmetric versions of these cycloaddition reactions are also known. Further manipulation of the cycloaddition products afforded interesting compounds that are useful synthons and building blocks in natural product synthesis and asymmetric synthesis.
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Cite this article as:
Lee W.M. Albert, Chan H. W., Zhang K. H. and Xia F. P., Sulfonate and Sulfonamide Activated Olefins and Acetylenes in [4+2] Cycloaddition Reactions, Current Organic Chemistry 2003; 7 (6) . https://dx.doi.org/10.2174/1385272033486800
DOI https://dx.doi.org/10.2174/1385272033486800 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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