129017-77-2Relevant academic research and scientific papers
Highly enantioselective synthesis of multifunctionalized allylic building blocks via oxazaborolidine-catalyzed borane reduction
Byung, Tae Cho,Sung, Hye Shin
, p. 6959 - 6966 (2007/10/03)
A simple and convenient synthesis of optically active alkenyl β-hydroxy sulfides with high enantiomeric excess by CBS-oxazaborolidine- catalyzed borane reduction of the corresponding β-keto sulfides and its application to synthesis of chiral alkenic diols have been established.
Asymmetric induction in Darzens condensation by means of (-)-8-phenylmenthyl and (-)-menthyl auxiliaries
Takagi, Ryukichi,Kimura, Jyunji,Shinohara, Yoshihiro,Ohba, Yuko,Takezono, Kyoko,Hiraga, Yoshikazu,Kojima, Satoshi,Ohkata, Katsuo
, p. 689 - 698 (2007/10/03)
Asymmetric Darzens condensation of benzaldehyde and various ketones has been investigated. The condensation of acetophenone, propiophenone and symmetric ketones with (-)-8-phenylmenthyl halogenoacetates 3a,b afforded the corresponding glycidic esters cis-12, cis-13 and 15-19 in 77-96% de, respectively, as the major products. Aza-Darzens condensation between N-benzylideneaniline and 3a occurred to give the trans-aziridine 21 as the major isomer in >85% de. The stereochemistry of the major diastereoisomers of cis-12 and 18 was confirmed by their conversion into the known optically active diols 22 and 24. The configuration of the major product of cis-12 was determined to be 2R,3R and that of 18 to be 2R. The geometric and disastereofacial selectivities were understandable in terms of the open-chain or non-chelated antiperiplanar transition state model in the initial aldol-type reaction.
Asymmetric epoxidation of chiral allylic alcohols
Warmerdam, Erwin G.J.C.,Van Den Nieuwendijk, Adrianus M.C.H.,Brussee, Johannes,Kruse, Chris G.,Van Der Gen, Arne
, p. 2539 - 2550 (2007/10/03)
Two series of chiral allylic alcohols, derived from α,β-unsaturated cyanohydrins, were subjected to asymmetric epoxidation under a variety of conditions. Both achiral (organic peracid, metal-catalyzed peroxide) and chiral (Sharpless titanium-tartrate syst
A convenient synthesis of vinyl epoxides from glycidic esters via α-hydroxy-β,γ-unsaturated esters
Bhattacharya,Shah,Vankar,Vankar
, p. 2405 - 2414 (2007/10/02)
Glycidic esters, upon isomerisation with BF3.ET2O yield α-hydroxy-β,γ-unsaturated esters. These are then reduced with LiAlH4 to vicinal diols which are converted to vinyl epoxides in two steps.
Conformationally restricted leukotriene antagonists. Asymmetric synthesis of a nor-leukotriene D4 analog. II1
Sabol,Cregge
, p. 27 - 30 (2007/10/02)
Chiral diol 5 is prepared from cyclohexanone and used in the asymmetric synthesis of nor-leukotriene D4 analog 1.
