2-(Phenylsulfonyl)-1,3-dienes as versatile synthons in organic transformations. Multicoupling reagents and Diels-Alder dienes with a dual electron demand

Unravelling the Synthesis and Chemistry of Stable, Acyclic, and Double‐Deficient 1,3‐Butadienes: An endo‐Selective Diels–Alder Route to Hedgehog Pathway Inhibitors

“…Padwa et al developed a multistep synthesis of 2,4‐bis‐sulfonyl 1,3‐butadienes ( 6 , Figure ) . The high electrophilicity of the terminal olefin in 6 and the sulfone being a leaving group induce further nucleophilic additions and the tendency of dienes 6 to follow dimeric cycloaddition in the presence of unreactive dienophiles; these were the main factors that limited a further exploitation of these dienes as viable building blocks.…”

“…McIntosh, Bäckvall and Spino's groups synthesized and explored the dienes 4 (Figure ) bearing only one electron‐withdrawing group in the Diels–Alder cycloaddition reactions . However, these dienes were prone to nucleophilic additions and undesired dimeric cycloadditions . In particular, dienes with an ester moiety had to be generated in situ for any further transformation .…”

Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products

“…A Lewis acid-mediated Diels–Alder reaction between diene 42 and methyl crotonate was then used to access cyclohexene 43 [ 20 ]. This reaction is notable for being an uncommon example of a [4 + 2] cycloaddition involving reaction partners that are both electron-deficient [ 21 ]. An additional complicating factor is the reluctance of crotonates to participate as dienophiles.…”

Regioselective addition reactions of 3-phenylsulfonyl-2-trifluoromethyl-1,3-butadiene with nucleophiles

“…Sulfur-substituent within the diene unit, in particular, not only increases the reactivity of the diene but also adds control to the regioselectivity of the cycloaddition or addition reaction [7,8]. Numerous reactions related to the sulfur-substituted 1,3-butadienes have been well established in the previous literatures [9][10][11][12]. In the past several decades, much effort has been devoted to introduce the trifluoromethyl functionality into organic molecules because of the dramatic effects of functionality on their structure stability and reactivity of the resulting compounds [13][14][15][16][17].…”