1,3-Asymmetric induction in electrophilic addition onto homoallylsilanes. An approach towards the total synthesis of (+/−)-kumausyne

Efficiency of Acid‐ and Mercury‐Catalyzed Cyclization Reactions in the Synthesis of Tetrahydrofurans from Allylsilyl Alcohols

“…However, with HgCl 2 , no cyclization products were obtained. In contrast to the results reported by Landais and co‐workers, thestereoselectivity of this kinetically controlled mercury‐catalyzed cyclization reaction is not affected by the nature of the mercury salt, nor by the temperature of the reaction 8…”

“…Among others,7 a commonly employed approach is the mercury‐catalyzed cyclization reaction. It has been reported that the stereoselectivity of mercury‐catalyzed cyclization reactions depends on several factors, such as the nature of the mercury salt,8 the structure of the unsaturated alcohol,9 and the presence or not of additives, such as water,10 in the reaction media (Scheme ).…”

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

“…In 1997, Landais' group approached the total synthesis of (±)-trans-kumausyne (403) via another strategy featuring the construction of tetrahydrofurans in good yield and diastereoselectivities with excellent 1,3-stereocontrol using electrophilic 5-exo-trig cyclizations of 2-silyl-4-alkenols. 455 The synthesis led to the formation of four chiral centers with excellent diastereoselectivities. Chandler and Phillips later described a different, concise 19-step synthesis of (±)-403 in 2005.…”

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

“…It had been cited in many publications that the stereoselectivity of products formed due to Hg(II)-salt-mediated cyclization reactions of alkene-alcohol derivatives depends on several factors: the nature of the Hg(II) salts [ 46 ], the starting materials [ 47 ], and the effect of H 2 O (protic solvent) in the reaction media [ 48 ].…”