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Volumn 7, Issue 12, 2005, Pages 2305-2308

2-Ene-1,4-diols by dimerization of terminal epoxides using hindered lithium amides

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBENOID; EPOXIDE; ETHER DERIVATIVE; LITHIUM DERIVATIVE; MANNITOL;

EID: 20544464926     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050402h     Document Type: Article
Times cited : (48)

References (44)
  • 2
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    • Grundmann, C. Ann. 1938, 536, 29-36.
    • (1938) Ann. , vol.536 , pp. 29-36
    • Grundmann, C.1
  • 5
    • 2542569635 scopus 로고    scopus 로고
    • For a recent example in synthesis, see: Li, G.-Y.; Che, C.-M. Org. Lett. 2004, 6, 1621-1623.
    • (2004) Org. Lett. , vol.6 , pp. 1621-1623
    • Li, G.-Y.1    Che, C.-M.2
  • 20
    • 20544434657 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 21
    • 20544435638 scopus 로고    scopus 로고
    • note
    • The (E)-meso-enediol was also observed to a lesser extent (∼9%, ref 7b), but the corresponding enediol was not observed in our dimerization of tert-butyloxirane.
  • 22
    • 0033603429 scopus 로고    scopus 로고
    • For examples of the uses of symmetric 2-ene-1,4-diols in total synthesis, see: (a) Masaki, Y.; Arasaki, H.; Itoh, A. Tetrahedron Lett. 1999, 40, 4829-4832.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4829-4832
    • Masaki, Y.1    Arasaki, H.2    Itoh, A.3
  • 30
    • 20544448402 scopus 로고    scopus 로고
    • note
    • 2; EtOAc/petrol) to give the enediols.
  • 31
    • 20544447907 scopus 로고    scopus 로고
    • note
    • LTMP precipitated from the hexane/t-BuOMe mixture; however, upon addition of the epoxide, the solution became homogeneous (this did not occur at higher reaction concentrations and was detrimental to the yield).
  • 33
    • 20544444152 scopus 로고    scopus 로고
    • note
    • The (E)-olefin geometry of 3a was confirmed by X-ray crystallography; see Supporting Information.
  • 35
    • 20544437587 scopus 로고    scopus 로고
    • note
    • The (E)-olefin geometry of 6 was confirmed by comparison with an authentic sample synthesized by 1,6-bis-trityl protection of (E)-3,4-dideoxy-D-mannitol (ref 14a).
  • 36
    • 0346051195 scopus 로고
    • Made by deprotonation of the corresponding commercially available amine with n-BuLi/TMEDA (1:1); see: Kopka, I. E.; Fataftah, Z. A.; Rathke, M. W. J. Org. Chem. 1987, 52, 448-450.
    • (1987) J. Org. Chem. , vol.52 , pp. 448-450
    • Kopka, I.E.1    Fataftah, Z.A.2    Rathke, M.W.3
  • 37
    • 20544462521 scopus 로고    scopus 로고
    • note
    • Under these conditions this base remains in solution, whereas LTMP precipitates, which results in longer reaction times and diminished yields. Application of these conditions to (R)-cyclohexyl oxirane did not lead to an improvement in yield or E:Z selectivity.
  • 40
    • 20544459754 scopus 로고    scopus 로고
    • note
    • 2O)).
  • 41
    • 0001081924 scopus 로고    scopus 로고
    • For an asymmetric synthesis of D-altritol based on a related strategy, see: Evans, P. A.; Murthy, V. S. J. Org. Chem. 1998, 63, 6768-6769.
    • (1998) J. Org. Chem. , vol.63 , pp. 6768-6769
    • Evans, P.A.1    Murthy, V.S.2
  • 44
    • 20544437345 scopus 로고    scopus 로고
    • note
    • 2O)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.