83334-11-6Relevant articles and documents
Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone
Athawale, Paresh R.,Zade, Vishal M.,Rama Krishna, Gamidi,Reddy, D. Srinivasa
, p. 6642 - 6647 (2021/09/02)
A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.
Copper-catalyzed γ-selective and stereospecific allyl-aryl coupling between (Z)-acyclic and cyclic allylic phosphates and arylboronates
Ohmiya, Hirohisa,Yokokawa, Natsumi,Sawamura, Masaya
supporting information; experimental part, p. 2438 - 2440 (2010/07/10)
A Cu-catalyzed allyl-aryl coupling reaction between (Z)-acyclic or cyclic allylic phosphates and arylboronates proceeds with excellent γ-E-selectivity and 1,3-anti chirality transfer, which gives the corresponding coupling products with benzylic and allylic stereogenic centers. The wide availability and easy-to-handle nature of arylboronates, the inexpensiveness of the Cu catalyst system, and the high regio- and stereoselectivities are attractive features of this protocol.
Stereochemistry and mechanism of vinyl-migrating [1,2]-Wittig rearrangement of α-lithioalkyl vinyl ethers
Tomooka, Katsuhiko,Inoue, Tadashi,Nakai, Takeshi
, p. 418 - 419 (2007/10/03)
Enantiomerically defined α-stannylalkyl or α-methylbenzyl vinyl ethers, when treated with butyllithium, are shown to undergo the 1,2-vinyl migration to afford the allylic alcohols in almost racemic form in low or high yield, respectively, thereby proposin
