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Volumn 56, Issue 3, 2017, Pages 786-790

Stereodivergent Olefination of Enantioenriched Boronic Esters

Author keywords

alkenes; boron; isomers; oxidation; selenium

Indexed keywords

BORON; CATALYSTS; CHEMICAL REACTIONS; ISOMERS; OLEFINS; OXIDATION; PLANTS (BOTANY); SELENIUM; STEREOCHEMISTRY; STEREOSELECTIVITY; TRANSITION METALS;

EID: 85006741629     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201610387     Document Type: Article
Times cited : (55)

References (60)
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    • Where possible, E, Z, ratios were determined using the following method, Analysis of purified materials by HPLC and GC gave, E, Z, ratios in good agreement with those determined from NMR analysis of the crude material
    • Where possible E/Z ratios were determined using the following method: T. D. W. Claridge, S. G. Davies, M. E. C. Polywka, P. M. Roberts, A. J. Russell, E. D. Savory, A. D. Smith, Org. Lett. 2008, 10, 5433–5436. Analysis of purified materials by HPLC and GC gave E/Z ratios in good agreement with those determined from NMR analysis of the crude material.
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    • Claridge, T.D.W.1    Davies, S.G.2    Polywka, M.E.C.3    Roberts, P.M.4    Russell, A.J.5    Savory, E.D.6    Smith, A.D.7
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    • It is preferable to utilize bromides because LiI (generated in situ by elimination of tBuI) can have a detrimental effect upon the E/Z selectivity of the selenium-mediated coupling process.
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    • 2,2,2-Trifluoroethanol proved essential for obtaining high diastereoselectivity in the selenation of trisubstituted vinyl boronate complexes.
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    • The two barriers refer to elimination from each of the two possible diastereomers at selenium.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.