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Volumn 8, Issue 15, 2006, Pages 3251-3254

Synthesis of pyrrolidines via palladium(II)-catalyzed aerobic oxidative carboamination of butyl vinyl ether and styrenes with allyl tosylamides

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMIDE; PALLADIUM; PYRROLIDINE DERIVATIVE; STYRENE DERIVATIVE; VINYL DERIVATIVE; VINYL ETHER;

EID: 33746917969     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061057e     Document Type: Article
Times cited : (93)

References (42)
  • 10
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    • II. For leading references, see: (a) Bäckvall, J.-E. Acc. Chem. Res. 1983, 16, 335-342.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 335-342
    • Bäckvall, J.-E.1
  • 12
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    • Intramolecular oxidative amination methods benefit from significant entropic advantage, and numerous examples are known. These reactions continue to be the subject of active interest. For leading references, see: (a) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444-2451.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 2444-2451
    • Hegedus, L.S.1    McKearin, J.M.2
  • 23
    • 33845280828 scopus 로고
    • Pd-catalyzed methods for the carboamination of alkenes are known, but they generally feature intramolecular C-N bond formation. For leading references, see: (a) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z,-i. J. Am. Chem. Soc. 1988, 110, 3994-4002.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3994-4002
    • Tamaru, Y.1    Hojo, M.2    Higashimura, H.3    Yoshida, Z.-I.4
  • 27
    • 33746893264 scopus 로고    scopus 로고
    • Ref 5g
    • (e) Ref 5g.
  • 30
    • 23044462967 scopus 로고    scopus 로고
    • Oshima et al. also described the oxidative coupling of allyl alcohols and vinyl ethers to produce tetrahydrofuran derivatives (ref 8). While the present work was in progress, the groups of Morken and Hosokawa reported important advances in reactions of allyl alcohols, including diastereoselective transformations and catalytic aerobic oxidation procedures, respectively. (a) Evans, M. A.; Morken, J. P. Org. Lett. 2005, 7, 3367-3370.
    • (2005) Org. Lett. , vol.7 , pp. 3367-3370
    • Evans, M.A.1    Morken, J.P.2
  • 32
    • 0025942580 scopus 로고
    • Oshima-like oxidative coupling of allyl alcohols and vinyl ethers and related reactions have been applied to the synthesis of natural products. For examples, see: (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815-7816.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7815-7816
    • Larock, R.C.1    Lee, N.H.2
  • 37
    • 33644645936 scopus 로고    scopus 로고
    • For a recent study into the role of molecular sieves in palladium-catalyzed aerobic oxidation reactions, see: Steinhoff, B. A.; King, A. E.; Stahl, S. S. J. Org. Chem. 2006, 71, 1861-1868.
    • (2006) J. Org. Chem. , vol.71 , pp. 1861-1868
    • Steinhoff, B.A.1    King, A.E.2    Stahl, S.S.3
  • 38
    • 33746926592 scopus 로고    scopus 로고
    • note
    • Abbreviations: dpp = 4,7-diphenyl-1,10-phenanthroline, IMes = 1,3-di(2,4,6-trimethylphenyl)imidazoline-2-ylidene, COD = 1,5-cyclooctadiene, TFA = trifluoroacetate.
  • 39
    • 33746902629 scopus 로고    scopus 로고
    • note
    • Significantly reduced yields are observed for reactions conducted in acetonitrile.
  • 40
    • 0033599513 scopus 로고    scopus 로고
    • For prior examples of COD and methyl acrylate as additives in palladium-catalyzed reactions, see: (a) Nishimura, T.; One, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645-2646.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2645-2646
    • Nishimura, T.1    One, K.2    Uemura, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.