113625-73-3Relevant academic research and scientific papers
Stereoinversion of Stereocongested Carbocyclic Alcohols via Triflylation and Subsequent Treatment with Aqueous N,N-Dimethylformamide
Ochiai, Hidenori,Niwa, Takashi,Hosoya, Takamitsu
supporting information, p. 5982 - 5985 (2016/12/09)
A convenient method for the stereoinversion of secondary alcohols, applicable to stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethylformamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.
Asymmetric synthesis of O-protected acyloins using enoate reductases: Stereochemical control through protecting group modification
Winkler, Christoph K.,Stueckler, Clemens,Mueller, Nicole J.,Pressnitz, Desiree,Faber, Kurt
experimental part, p. 6354 - 6358 (2011/02/24)
O-Protected cyclic acyloins were obtained in nonracemic form through asymmetric bioreduction of α,β-unsaturated alkoxy ketones by using 11 different enoate reductases from the "Old Yellow Enzyme" family. The stereochemical outcome of the biotransformation could be switched by variation of the O-protecting group or by the ring size of the substrate, which allows access to both stereoisomers in up to >97 % ee Whereas α-alkoxy enones were readily accepted as substrates, β-analogs were not converted. Overall, α-alkoxy enones represent a novel type of substrate for flavin-dependent ene-reductases. Copyright
CpRuIIPF6/quinaldic acid-catalyzed chemoselective allyl ether cleavage. A simple and practical method for hydroxyl deprotection
Tanaka, Shinji,Saburi, Hajime,Ishibashi, Yoshitaka,Kitamura, Masato
, p. 1873 - 1875 (2007/10/03)
Matrix presented. A cationic CpRuII complex in combination with quinaldic acid shows high reactivity and chemoselectivity for the catalytic deprotection of hydroxyl groups protected as allyl ethers. The catalyst operates in alcoholic solvents without the need for any additional nucleophiles, satisfying the practical requirements of operational simplicity, safety, and environmental friendliness. The wide applicability of this deprotection strategy to a variety of multifunctional molecules, including peptides and nucleosides, may provide new opportunities in protective group chemistry.
Chiral synthesis via organoboranes. 45. Asymmetric hydroboration of 1-cyclopentenol derivatives using diisopinocampheylborane. Synthesis of optically active cyclopentane-1,2-diol derivatives of high optical purity
Brown, Herbert C.,Murali, Dhanabalan,Singaram, Bakthan
, p. 116 - 121 (2007/10/03)
The asymmetric hydroboration of 1-cyclopentenol derivatives, such as ethers, acetate, silyl ether and borinate, was investigated using diisopinocampheylborane, dIpc2BH. The product trialkylboranes were treated with excess of acetalde
Regiochemical Control of the Ring-Opening of Epoxides by Means of Chelating Processes, 13. Synthesis and Ring-Opening Reactions of the Diastereoisomeric cis- and trans-Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran
Crotti, Paolo,Bussolo, Valeria Di,Favero, Lucilla,Macchia, Franco,Pineschi, Mauro
, p. 1675 - 1686 (2007/10/03)
The regiochemical outcome of the ring-opening of epoxides bearing remote polar functionalities has been established in the case of carbocyclic (1 and 2) and the corresponding furanosidic (3 and 4) title epoxides. Under standard conditions, the regioisomeric C-1 products are the sole (from trans epoxides 2 and 4) or predominant (from cis epoxides 1 and 3) ring-opening products. However, under chelating conditions, and only in the case of the cis epoxides 1 and 3, a consistent increase in C-2 selectivity is unexpectedly observed. - Keywords: Epoxides; Regioselectivity; Nucleophilic additions; Synthetic methods
Carbocyclic phosphonate-based nucleotide analogs related to PMEA II. Racemic cis-configured derivatives
Liboska, Radek,Masojidkova, Milena,Rosenberg, Ivan
, p. 778 - 790 (2007/10/03)
Racemic N-(cis-2-phosphonomethoxycycloalkyl) derivatives of heterocyclic bases, a novel type of nucleotide analogs related to 9-(2-phosphonomethoxyethyl)adenine (PMEA), are reported. The synthesis of adenine-(6a, 6b), uracil-(6c) and cytosine-(6d) contain
Enzymatic hydrolysis and esterification. Routes to optically pure cyclopentanols
Seemayer, R.,Schneider, M. P.
, p. 171 - 174 (2007/10/02)
Using an esterhydrolase from Pseudomonas sp. (SAM II), a series of optically pure cyclopentanols 1-4 was prepared by enzymatic hydrolysis of their corresponding acetates.Using the same enzyme, these cyclopentanols were esterified by enol esters as acyl do
Hydroboration of Vinyl Ethers with Diisopinocampheylborane
Peterson, Paul E.,Stepanian, Marshall
, p. 1903 - 1907 (2007/10/02)
The reactions of diisopinocampheylborane with cyclic vinyl ethers having an exocyclic oxygen and with acyclic vinyl ethers having groups of varying size attached to oxygen were explored.Evidence of some interaction of the bulkier vinyl ethers with diisopinocampheylborane was obtained, but high enantiomeric excesses were not found.However, the hydroboration-oxidation of benzyl or diphenylmethyl vinyl ethers, followed by cleavage, is a practical route to partially resolved diols.
