메뉴 건너뛰기




Volumn 8, Issue 12, 2006, Pages 2531-2534

A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPENYLUREA; 2-PROPENYLUREA; DRUG DERIVATIVE; IMIDAZOLIDINE DERIVATIVE; PALLADIUM; UREA;

EID: 33745544284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060707b     Document Type: Article
Times cited : (70)

References (32)
  • 15
    • 1242269280 scopus 로고    scopus 로고
    • For related reactions that provide tetrahydrofuran products, see: (a) Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 1620-1621
    • Wolfe, J.P.1    Rossi, M.A.2
  • 17
    • 0001835856 scopus 로고
    • For a two-step carboamination strategy involving ureidomercuration followed by radical-mediated alkylation, see: Danishefsky, S.; Taniyama, E.; Webb, R. R., II. Tetrahedron Lett. 1983, 24, 11-14.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 11-14
    • Danishefsky, S.1    Taniyama, E.2    Webb II, R.R.3
  • 18
    • 33845280828 scopus 로고
    • Tamaru has described Pd(II)-catalyzed Wacker-type carbonylation reactions of N-allylureas and O-allylcarbamates that effect ring closure with concomitant C-C bond formation to afford imidazolidin-2-ones and oxazolidin-2-ones bearing carbonyl functionality at C-4. 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
  • 20
    • 33745580578 scopus 로고    scopus 로고
    • note
    • Xantphos = 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene; dppe = 1,2-bis(diphenylphosphino)ethane; dppf = 1,1′-bis(diphenylphosphino) ferrocene.
  • 21
    • 33745551291 scopus 로고    scopus 로고
    • note
    • t-Bu in the absence of Pd.
  • 22
    • 33745557387 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis.
  • 23
    • 33745531968 scopus 로고    scopus 로고
    • note
    • tBu in the absence of Pd.
  • 24
    • 33745525221 scopus 로고    scopus 로고
    • note
    • Substrates 4-7, 20, 22, 25, and 27 were obtained in 79-97% yield from treatment of the corresponding allylamine with the appropriate isocyanate as described above.
  • 28
    • 27544506294 scopus 로고    scopus 로고
    • Attempts to transform substrates bearing unprotected N3 moieties led to the formation of products resulting from tandem N-arylation and carboamination in low yield (ca. 30%). For a related reaction of aliphatic amines, see: Yang, Q.; Ney, J. E.; Wolfe, J. P. Org. Lett. 2005, 7, 2575-2578.
    • (2005) Org. Lett. , vol.7 , pp. 2575-2578
    • Yang, Q.1    Ney, J.E.2    Wolfe, J.P.3
  • 29
    • 33745532362 scopus 로고    scopus 로고
    • note
    • 1H NMR COSY and nOe experiments. See the Supporting Information for complete details of stereochemical assignments.
  • 30
    • 20944448962 scopus 로고    scopus 로고
    • 2Me-catalyzed carboaminations of N-(p-methoxyphenyl)-2-(cyclopent-2-enylethyl)amine. See: Ney, J. E.; Wolfe, J. P. J. Am. Chem. Soc. 2005, 127, 8644-8651.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 8644-8651
    • Ney, J.E.1    Wolfe, J.P.2
  • 31
    • 33745569321 scopus 로고    scopus 로고
    • note
    • A small amount of N-(cyclohex-2-enyl)aniline was observed as a side product in this reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.