146388-52-5Relevant academic research and scientific papers
Stereodivergent Access to Enantioenriched Epoxy Alcohols with Three Stereogenic Centers via Ruthenium-Catalyzed Transfer Hydrogenation
Zhao, Zhifei,Bagdi, Prasanta Ray,Yang, Shuang,Liu, Jinggong,Xu, Weici,Fang, Xinqiang
, p. 5491 - 5494 (2019/08/01)
The resolution technique of stereodivergent reaction on racemic mixtures (stereodivergent RRM) was employed for the first time in ruthenium complex catalyzed transfer hydrogenation of racemic epoxy ketones, providing a new and very simple method that allows access to enantioenriched epoxy alcohols with three stereogenic centers in a one-step fashion. The protocol features simple reaction conditions, practical operation, ability to scale up, and broad group tolerance.
Asymmetric epoxidation of styrene derivatives by styrene monooxygenase from Pseudomonas sp. LQ26: Effects of α- And β-substituents
Lin, Hui,Liu, Yan,Wu, Zhong-Liu
experimental part, p. 134 - 137 (2011/04/27)
Recombinant Escherichia coli expressing a styrene monooxygenase, StyAB2, from Pseudomonas sp. LQ26 was applied to synthesize a range of chiral epoxides from conjugated styrene derivatives with excellent (>99%) enantioselectivity in most cases. The substrate preference was studied with a special focus on the steric effect of α- and β-substituents.
Mechanistic implications of pseudo zero order kinetics in kinetic resolutions
Blackmond, Donna G.,Hodnett, Neil S.,Lloyd-Jones, Guy C.
, p. 7450 - 7451 (2007/10/03)
This work provides simulations as well as experimental results from kinetic resolutions to demonstrate that a constant product enantioselectivity versus conversion profile in kinetic resolution is not a general consequence of pseudo zero order kinetics in
Enantioselective epoxidation with chiral MnIII(salen) catalysts: Kinetic resolution of aryl-substituted allylic alcohols
Adam,Humpf,Roschmann,Saha-Moeller
, p. 5796 - 5800 (2007/10/03)
A set of aryl-substituted allylic alcohols rac-2 has been epoxidized by chiral Mn(salen*) complexes 1 as the catalyst and iodosyl benzene (PhIO) as the oxygen source. Whereas one enantiomer of the allylic alcohol 2 is preferentially epoxidized to give the threoor cis-epoxy alcohol 3 (up to 80% ee) as the main product (dr up to >95:5), the other enantiomer of 2 is enriched (up to 53% ee). In the case of 1,1-dimethyl-1,2-dihydronaphthalen-2-ol (2c), the CH oxidation to the enone 4c proceeds enantioselectively and competes with the epoxidation. The absolute configurations of the allylic alcohols 2 and their epoxides 3 have been determined by chemical correlation or CD spectroscopy. The observed diastereo- and enantioselectivities in the epoxidation reactions are rationalized in terms of a beneficial interplay between the hydroxy-directing effect and the attack along the Katsuki trajectory.
Synthesis of chiral epoxy alcohols by use of baker's yeast
Takeshita,Akutsu
, p. 1381 - 1384 (2007/10/02)
Synthesis of optically active 3,4-epoxy-4-phenyl-2-butanols, which are expected to be useful intermediates for the synthesis of biologically active compounds such as β-blocker, was achieved by asymmetric reduction of 3,4-epoxy-4-phenyl-2-butanone with baker's yeast.
Organoaluminum-catalyzed rearrangement of epoxides a facile route to the synthesis of optically active β-siloxy aldehydes
Maruoka, Keiji,Ooi, Takashi,Nagahara, Shigeru,Yamamoto, Hisashi
, p. 6983 - 6998 (2007/10/02)
A new, stereocontrolled rearrangement of epoxy silyl ethers leading to β-siloxy aldehydes has been effected with stoichiometric use of exceptionally bulky, oxygenophilic methylaluminum bis(4-bromo-2,6-di-trert-butylphenoxide) (MABR) under mild conditions. Used in combination with the Sharpless asymmetric epoxidation of allylic alcohols, this rearrangement represents a new approach to the synthesis of various optically active β-hydroxy aldehydes, useful intermediates in natural product synthesis. The modified organoaluminum reagent, MABR is also applicable to the transformation of a variety of simple epoxides to carbonyl compounds with high efficiency and selectivity. Further, the catalytic version for the rearrangement of epoxy silyl ethers as well as simple epoxides has been newly devised. The scope and limitation of this catalytic method has been clarified with various epoxy substrates.
A Novel Probe for Free Radicals featuring Epoxide Cleavage
Dickinson, Julia M.,Murphy, John A.,Patterson, Christopher W.,Wooster, Nicholas F.
, p. 1179 - 1184 (2007/10/02)
This paper describes the identification of carbon-carbon bond cleavage within a defined range of epoxides as being a reaction type which is specifically diagnostic of free radicals adjacent to the epoxide.The speed of the epoxide cleavage is greater than
