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Volumn 13, Issue 20, 2011, Pages 5460-5463

Stereoselective rhodium-catalyzed amination of alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; RHODIUM;

EID: 80054715442     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2021516     Document Type: Article
Times cited : (82)

References (58)
  • 42
    • 0032509407 scopus 로고    scopus 로고
    • Desulfonylation by metal reduction was reported to produce 2-phenylaziridine, although this reaction was either contaminated with ring-opened product or proceeded in low yield (40%). For further details, see
    • Desulfonylation by metal reduction was reported to produce 2-phenylaziridine, although this reaction was either contaminated with ring-opened product or proceeded in low yield (40%). For further details, see: Alonso, D. A.; Andersson, P. G. J. Org. Chem. 1998, 63, 9455-9461
    • (1998) J. Org. Chem. , vol.63 , pp. 9455-9461
    • Alonso, D.A.1    Andersson, P.G.2
  • 51
    • 38349004623 scopus 로고    scopus 로고
    • Such a strategy has been previously reported by Dodd and Dauban using a chiral sulfonimidamide (prepared in 23% yield via fractional recrystallization of diastereomers) for rhodium-catalyzed benzylic and allylic C-H insertion reactions; see: The scope was however limited when similar chiral sulfonimidamides were used in aziridination reactions. If acrylate substrates produced the desired aziridine with 94% de, for styrene, only 65% de was obtained. See ref 11d and 11e for details
    • Such a strategy has been previously reported by Dodd and Dauban using a chiral sulfonimidamide (prepared in 23% yield via fractional recrystallization of diastereomers) for rhodium-catalyzed benzylic and allylic C-H insertion reactions; see: Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343. The scope was however limited when similar chiral sulfonimidamides were used in aziridination reactions. If acrylate substrates produced the desired aziridine with 94% de, for styrene, only 65% de was obtained. See ref 11d and 11e for details
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 343
    • Liang, C.1    Collet, F.2    Robert-Peillard, F.3    Müller, P.4    Dodd, R.H.5    Dauban, P.6
  • 52
    • 0025068753 scopus 로고
    • (R)-1-Phenyl-2,2,2-trichloroethanol was readily produced in 94% yield and 95% ee on 50 mmol scale via catalytic CBS-reduction, according to literature procedure: See Supporting Information for details
    • (R)-1-Phenyl-2,2,2-trichloroethanol was readily produced in 94% yield and 95% ee on 50 mmol scale via catalytic CBS-reduction, according to literature procedure: Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611. See Supporting Information for details
    • (1990) Tetrahedron Lett. , vol.31 , pp. 611
    • Corey, E.J.1    Bakshi, R.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.