New amine-stabilized deuterated borane–tetrahydrofuran complex (BD3–THF): convenient reagent for deuterium incorporations

Todd, Robert; Hossain, M. Mahmun; Josyula, Kanth V. B.; Gao, Peng; Kuo, John S.; Tan, Chaowei

doi:10.1016/j.tetlet.2007.01.134

Cited by 11 publications

(6 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To a solution of sodium hydride (60% in mineral oil, 1 equiv) in THF (7 mL) was added di- tert -butyl malonate (1 equiv), and the solution was stirred until gas evolution was complete. To the reaction mixture was added alkyl halide (1 equiv), and the solution was stirred until reaction completion was determined by TLC analysis . The reaction was quenched with saturated NH 4 Cl (6 mL) at 0 °C, phases were separated, and aqueous phase was extracted EtOAc (2 × 15 mL).…”

Section: Experimental Sectionmentioning

confidence: 99%

“…To the reaction mixture was added alkyl halide (1 equiv), and the solution was stirred until reaction completion was determined by TLC analysis. 16 The reaction was quenched with saturated NH 4 Cl (6 mL) at 0 °C, phases were separated, and aqueous phase was extracted EtOAc (2 × 15 mL). The combined organic phases were dried over MgSO 4 and concentrated.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 1 more Smart Citation

Enantioselective Desymmetrization of Diesters

Wilent

Petersen

2014

J. Org. Chem.

View full text Add to dashboard Cite

The desymmetrization of prochiral diesters with a chiral phosphoric acid catalyst to produce highly enantioenriched lactones in excellent yield is reported. The process is easily scaled and accommodates a variety of substitution patterns, many of which result in the generation of an enantioenriched all-carbon quaternary center. Manipulation of lactone product to useful small building blocks is also described.

show abstract

Section: Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Enantioselective Desymmetrization of Diesters

Wilent

Petersen

2014

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…27 Hydroboration and oxidation of 15 gave the anti-Markovnikov alcohol 16 . 28 Protection of the alcohol was done using TBSCl in basic conditions 29 to generate bromide 18 . Conversion of the aryl bromide of silyl ether 18 into the corresponding carboxylic acid ( 5z ) was achieved by lithium-halogen exchange using n -butyl lithium followed by purging the mixture with CO 2 gas.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis and biological evaluation of GPR55 agonists

Fakhouri

Cook

Al‐Huniti

et al. 2017

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

GPR55, a G protein-coupled receptor, is an attractive target to alleviate inflammatory and neuropathic pain and treat osteoporosis and cancer. Identifying a potent and selective ligand will aid to further establish the specific physiological roles and pharmacology of the receptor. Towards this goal, a targeted library of 22 compounds was synthesized in a modular fashion to obtain structure-activity relationship information. The general route consisted of coupling a variety of p-aminophenyl sulfonamides to isothiocyanates to form acylthioureas. For the synthesis of a known naphthyl ethyl alcohol motif, route modification led to a shorter and more efficient process. The 22 analogues were analyzed for their ability to serve as agonists at GPR55 and valuable information for both ends of the molecule was ascertained.

show abstract

“…For example, PhCH(OH)CD 3 can be prepared from the reaction of PhCHO with CD 3 MgI (prepared from CD 3 I and Mg)8 or the reaction of LiAlH 4 with PhC(O)CD 3 (prepared from PhCO 2 H and CD 3 Li);9 CH 3 (CH 2 ) 5 CH(OH)CDH 2 can be prepared from the reaction of CH 3 (CH 2 ) 5 CHCH 2 with BD 3 . THF followed by treatment with H 2 O 2 /NaOH 11. A more cost‐effective and time‐efficient approach to deuterium‐labeled alcohols involves metal‐catalyzed direct H/D exchange between alcohols and an appropriate deuterium source.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium‐Catalyzed Regioselective Deuteration of Alcohols at the β‐Carbon Position with Deuterium Oxide

Tse

Xue

Lau

et al. 2011

Chemistry A European J

View full text Add to dashboard Cite

A convenient method for regioselective H/D exchange between D(2)O and alcohols at the β-carbon position using the catalytic system [(p-cymene)RuCl(2)]/ethanolamine/KOH is described. This method is applicable for deuteration of both primary and secondary alcohols. The H/D exchange reactions proceed through an oxidation/modification/reduction reaction sequence. Alcohols are first temporarily oxidized to carbonyl compounds by the hydrogen transfer catalyst. The carbonyl compounds then undergo deuteration at the carbon adjacent to the carbonyl group by keto-enol tautomerization in the presence of D(2)O and a catalytic amount of base. The deuterated carbonyl compounds are then reduced to produce deuterated alcohols. In support of the reaction mechanism, a well-defined bimetallic ruthenium complex was isolated from the reaction of [{(p-cymene)RuCl(2)}(2)] with ethanolamine. The activity of this complex is similar to that of [{(p-cymene)RuCl(2)}(2)]/ethanolamine.

show abstract

New amine-stabilized deuterated borane–tetrahydrofuran complex (BD3–THF): convenient reagent for deuterium incorporations

Cited by 11 publications

References 8 publications

Enantioselective Desymmetrization of Diesters

Enantioselective Desymmetrization of Diesters

Design, synthesis and biological evaluation of GPR55 agonists

Ruthenium‐Catalyzed Regioselective Deuteration of Alcohols at the β‐Carbon Position with Deuterium Oxide

Contact Info

Product

Resources

About