221082-33-3Relevant academic research and scientific papers
Iridium-catalyzed enantioselective allylic substitution with aqueous solutions of nucleophiles
Sandmeier, Tobias,Goetzke, F. Wieland,Krautwald, Simon,Carreira, Erick M.
supporting information, p. 12212 - 12218 (2019/08/20)
The iridium-catalyzed asymmetric allylic substitution under biphasic conditions is reported. This approach allows the use of various unstable and/or volatile nucleophiles including hydrazines, methylamine, t-butyl hydroperoxide, N-hydroxylamine, α-chloroacetaldehyde and glutaraldehyde. This transformation provides rapid access to a broad range of products from simple starting materials in good yields and up to >99% ee and 20:1 d.r. Additionally, these products can be elaborated efficiently into a diverse set of cyclic and acyclic compounds, bearing up to four stereocenters.
Catalytic and asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement
Fukuda, Tsutomu,Irie, Ryo,Katsuki, Tsutomu
, p. 649 - 664 (2007/10/03)
Reaction of allyl aryl sulfides and α-diazoacetic acid esters in the presence of optically active Co(III)-salen complex (8-Br) provided 3- substituted 2-arylthio-4-pentenoic acid esters stereoselectively by way of enantioselective S-ylide formation and subsequent diastereoselective [2,3]sigmatropic rearrangement. For example, the reaction of cinnamyl phenyl sulfide and (-)-menthyl α-diazoacetate provided (-)-menthyl (2R,3S)-2- phenylthio-3-phenyl-4-pentenoate of 74% de preferentially.
Co(III)-salen catalyzed carbenoid reaction: Stereoselective [2,3]sigmatropic rearrangement of S-ylides derived from allyl aryl sulfides
Fukuda, Tsutomu,Katsuki, Tsutomu
, p. 3435 - 3438 (2007/10/03)
Allyl aryl sulfides and diazoacetic acid esters react in the presence of optically active Co(III)-salen complex (4) with good enantioselectivity, to give the [2,3]sigmatropic rearrangement products, 2-arylthio-3-aryl-4-pentenoic acid esters, via the corresponding S-ylides.
