62961-00-6Relevant articles and documents
Enzymatic kinetic resolution of chiral sulfoxides-an enantiocomplementary approach
Nosek, Vladimír,Mí?ek, Ji?í
supporting information, p. 10480 - 10483 (2019/09/07)
A new enzymatic assay for the preparation of chiral sulfoxides that is enantiocomplementary to the known (S)-enantiomer-reducing activity of methionine sulfoxide reductase A (MsrA) is described. To this end, we have utilized the enzyme DMSO reductase (DmsABC), recently discovered by us being highly upregulated in stationary phase E. coli bacteria.
Symmetric diarylsulfoxides as asymmetric sulfinylating reagents for dialkylmagnesium compounds
Ruppenthal, Simon,Brückner, Reinhard
, p. 897 - 910 (2015/01/30)
At -78 °C, primary dialkylmagnesium compounds reacted with diarylsulfoxides when 1.5 equiv of the dilithium salt of (S)-BINOL was added as a promotor. Alkyl aryl sulfoxides resulted in up to quantitative yield and with up to 97% ee. This demonstrates the feasibility of asymmetric sulfinylations by achiral sulfinylating agents (from the perspective of Alkyl2Mg) as well as the feasibility of asymmetric sulfoxide-magnesium exchanges (from the perspective of Ar2SO).
Chain Extension of Boronic Esters with Lithiooxiranes Generated by Sulfoxide-Metal Exchange - Stereocontrolled Access to 2°/2°, 2°/3°, and 3°/3° Vicinal Diols and Related Compounds
Alwedi, Embarek,Zakharov, Lev N.,Blakemore, Paul R.
, p. 6643 - 6648 (2016/02/19)
Lithiooxiranes [LiCR1(O)CR2R3, R1 = H, Me; R2/R3 = H/Ph, H/tBu, Me/Ph], generated by sulfoxide-lithium exchange from stereodefined sulfinyl epoxides (with use of PhLi or tBuLi, THF, at or below -90 °C), were employed for the stereospecific reagent-controlled homologation of boronic esters R0-Bpin (R0 = BnCH2, allyl, cHex, Ph). Addition of TBSOTf to the intermediate ate complexes gave β-silyloxyboronates that were converted to vicinal diol monosilyl ethers by oxidative work-up with aq. NaOOH. The 2°/2° (4-32 %, dr > 98:2), 2°/3° (21-66 %, dr ≥ 65:35), and 3°/3° (59-68 %, dr ≥ 95:5) contiguous stereodiad-containing compounds created in this manner were typically obtained in a highly stereocontrolled manner. In general, cis-sulfinyl epoxides afforded anti-like stereodiads, whereas trans-sulfinyl epoxides afforded syn-like stereodiads; however, as a result of its suspected configurational instability, LiCMe(O)CHPh gave anti-like 2°/3° motifs regardless of sulfinyl epoxide stereochemistry.