3839-31-4Relevant articles and documents
A Tandem Non-Aldol Aldol Mukaiyama Aldol Reaction
Jung, Michael E.,Van Den Heuvel, Alexandra
, p. 4705 - 4707 (2003)
(Equation presented) A new one-pot tandem aldol process is described in which a secondary epoxy silyl ether is converted into the 1,5-bis-silyloxy-3- alkanone in good yield. Thus, treatment of the epoxy silyl ether 8 with TBSOTf and base affords the silyl
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
supporting information, 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.
Synthesis of Alkyl Silanes via Reaction of Unactivated Alkyl Chlorides and Triflates with Silyl Lithium Reagents
Mallick, Shubhadip,Würthwein, Ernst-Ulrich,Studer, Armido
supporting information, p. 6568 - 6572 (2020/09/02)
The reaction of unactivated secondary and primary alkyl chlorides as well as primary alkyl triflates with silyl lithium reagents to access tetraorganosilanes is reported. These nucleophilic substitutions proceed in the absence of any transition metal catalyst under mild conditions in moderate to very good yields. The silyl lithium reagents are readily generated from the corresponding commercially available chlorosilanes. Enantioenriched secondary alkyl chlorides react with high stereospecificity under inversion of configuration.