448957-53-7Relevant academic research and scientific papers
Acid promoted cyclodehydration of amino alcohols with amide acetal
Hwang, Soonho,Park, Heemin,Kwon, Yongseok,Kim, Sanghee
, p. 60017 - 60024 (2015/02/19)
A convenient acid-promoted cyclization protocol for the formation of azaheterocycles from amino alcohols is described. The reaction involves the use of N,N-dimethylacetamide dimethyl acetal (DMADA) as the activating reagent of the hydroxyl group. Using this protocol, pyrrolidines or piperidines with various substituents can be synthesized in good to high yields.
Mild nonepimerizing N -alkylation of amines by alcohols without transition metals
Guerin, Claire,Bellosta, Veronique,Guillamot, Gerard,Cossy, Janine
supporting information; experimental part, p. 3534 - 3537 (2011/08/10)
A one-pot two-step sequence involving an oxidation/imine-iminium formation/reduction allowed the N-alkylation of amines by alcohols without any epimerization when optically active alcohols and amines are involved in the process.
METHOD OF HYDROBORATING ALCOHOLS AND REDUCING FUNCTIONAL GROUPS USING A RECYCLABLE FLUOROUS BORANE-SULFIDE
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Page 18; 28, (2010/02/06)
A method of hydroborating an alkene or alkyne, or reducing an organic functionality, oxidizing primary and secondary alcohols using a fluorous borane-sulfide is disclosed. The method includes regeneration and recycling the fluorous borane-sulfide.
A mechanistic alternative for the intramolecular hydroboration of homoallylic amine and phosphine borane complexes
Scheideman, Matthew,Shapland, Peter,Vedejs, Edwin
, p. 10502 - 10503 (2007/10/03)
Intramolecular hydroboration is demonstrated starting from homoallylic amine boranes upon activation by iodine. The process involves a B-iodoborane complex as the intermediate and may occur via internal displacement of iodide by the alkene to generate a cationic borane-alkene π-complex on the way to hydroboration products. The reaction can be carried out using a catalytic amount of iodine. Copyright
Tandem polar/radical crossover sequences for the formation of fused and bridged bicyclic nitrogen heterocycles involving radical ionic chain reactions, and alkene radical cation intermediates, performed under reducing conditions: Scope and limitations
Crich, David,Ranganathan, Krishnakumar,Neelamkavil, Santhosh,Huang, Xianhai
, p. 7942 - 7947 (2007/10/03)
It is demonstrated that phosphorylated forms of β-nitro alcohols provide an excellent means of entry into β-(phosphatoxy)alkyl radicals on exposure to tributyltin hydride and AIBN in benzene at reflux. These radicals then undergo heterolytic cleavage of t
Generation and trapping of alkene radical cations under nonoxidizing conditions: Formation of six-membered rings by exo- and endo-mode cyclizations
Crich, David,Neelamkavil, Santhosh
, p. 2573 - 2575 (2007/10/03)
(Matrix presented) It is demonstrated that alkene radical cations generated by the radical ionic fragmentation of β-(phosphatoxy)alkyl radicals undergo efficient nucleophilic capture by amines in either the 6-exo or 6-endo modes, leading to six-membered n
Fluorous dimethyl sulfide: A convenient, odorless, recyclable borane carrier
Crich, David,Neelamkavil, Santhosh
, p. 4175 - 4177 (2007/10/03)
(matrix presented) Borane gas and 2-(perfluorooctyl)ethyl methyl sulfide form a solid comprised of an approximately 1:1 mixture (fluorous BMS) of sulfide and the corresponding sulfide-borane. Fluorous BMS permits hydroboration of alkenes in a dichloromethane/perfluorinated hydrocarbon mixture with subsequent recycling of the fluorous sulfide by fluorous extraction. The use of fluorous BMS in the asymmetric reduction of ketones catalyzed by a chiral oxaborolidine catalyst, and in the reduction of other functional groups, is also reported.
