302934-10-7Relevant articles and documents
Remote stereocontrol by sulfinyl groups: Asymmetric alkylation of chiral 2-p-tolylsulfinyl benzyl carbanions
García Ruano, José L.,Aranda, M. Teresa,Puente, Margarita
, p. 10099 - 10104 (2007/10/03)
Alkylation reactions of the benzyllithiums derived from enantiomerically pure 2-p-tolylsulfinyl alkylbenzenes have been carried out with excellent yields and high de. A lithiation-substitution sequence, stereochemically controlled by a remote sulfoxide, accounts for the experimental results.
Highly stereoselective vinylogous pummerer reaction mediated by Me 3SiX
Garcia Ruano, Jose L.,Aleman, Jose,Aranda, M. Teresa,Arevalo, Maria J.,Padwa, Albert
, p. 19 - 22 (2007/10/03)
(Chemical Equation Presented) A highly stereoselective vinylogous Pummerer rearrangement involving 1,4-migration of the sulfinyl oxygen atom occurs when ortho-sulfinyl benzyl carbanions are treated with trimethylsilyl halides. The reaction proceeds in goo
Enantioselective generation of benzylic stereocenters mediated by a remote sulfoxide
Garcia Ruano, Jose L.,Carreno, M. Carmen,Toledo, Miguel A.,Aguirre, Jose M.,Aranda, M. Teresa,Fischer, Jean
, p. 2736 - 2737 (2007/10/03)
Ortho-Sulfinyl-substituted benzyllithium reagents react with aldehydes and ketones to afford, after desulfurization with Raney-Nickel, stereoselective access to benzylic stereocenters [Eq. (1)]. This is the first efficient asymmetric 1,4-induction with mediation by a sulfoxide group. LDA = lithium diisopropylamide; Tol = tolyl; TIPS = triisopropylsilyl.