113625-73-3Relevant articles and documents
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.
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.
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