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Volumn 48, Issue 28, 2007, Pages 4825-4829

Comparative approaches toward diamines containing spatially separated homobenzylic and benzylic nitrogen stereocenters

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; BENZYL DERIVATIVE; DIAMINE DERIVATIVE; NITROGEN DERIVATIVE; PHOSPHINE DERIVATIVE; RHENIUM;

EID: 34250030237     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.073     Document Type: Article
Times cited : (6)

References (46)
  • 2
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    • Lopez, P.; Siegmund, A.; Frohn, M.; Liu, L. Rishton, G. unpublished results.
  • 3
    • 34250018974 scopus 로고    scopus 로고
    • Frohn, M. J.; Hong, F.-T.; Liu, L.; Lopez, P.; Siegmund, A. C.; Tadesse, S.; Tamayo, N. WO 070932A2, 2005, Amgen Inc.
  • 4
    • 34250005595 scopus 로고    scopus 로고
    • note
    • ® (renal failure).
  • 5
    • 34250007272 scopus 로고    scopus 로고
    • note
    • Compounds 1 and 2 contain two stereogenic centers, whereas 3 contains one homobenzylic amine stereocenter and a benzylic quaternary center.
  • 7
    • 34250007816 scopus 로고    scopus 로고
    • note
    • Facile cleavage and recycling are the main advantages of this chiral auxiliary over the standard Evans' oxazolidinone system.
  • 9
    • 34250029136 scopus 로고    scopus 로고
    • note
    • Average of multiple runs.
  • 11
    • 34250025530 scopus 로고    scopus 로고
    • note
    • 80% of 9 isolated by crystallization. Additional 11% of 9 could be recovered from the mother liquors by column chromatography (91% yield total).
  • 12
    • 34249995874 scopus 로고    scopus 로고
    • note
    • Caution: Hydrazoic acid is a volatile and potentially explosive compound in a gaseous state. Handle with care. Avoid contact with heavy metal salts and alloys.
  • 13
    • 34250010738 scopus 로고    scopus 로고
    • note
    • First crop. Additional material could be recovered by chromatography of the mother liquors.
  • 17
    • 34249988092 scopus 로고    scopus 로고
    • note
    • O-Diphenylphosphinyl oxime. Unstable O-phosphinyl oximes (cf. Lopez, L.; Barrans, J. J. Chem. Soc., Perkin Trans. 1 1977, 1806-1811) rearrange thermally to N-phosphinyl imines via the radical mechanism (cf. Brown, C.; Hudson, R. F.; Maron, A.; Record, K. A. F. J. Chem. Soc., Chem. Commun. 1976, 663-664).
  • 18
    • 34249991056 scopus 로고    scopus 로고
    • note
    • Typical reaction time reported in Ref. 13 was 72 h at room temperature.
  • 19
    • 34250002406 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the major product was not assigned. However, the stereochemistry shown in Scheme 4 follows the direction of the induction from Ref. 13.
  • 22
    • 34250017574 scopus 로고    scopus 로고
    • note
    • 3 to mitigate these issues was not investigated.
  • 25
    • 1542375289 scopus 로고    scopus 로고
    • For recent reviews on aziridine chemistry, see:
    • For recent reviews on aziridine chemistry, see:. Hu X.E. Tetrahedron 60 (2004) 2701-2743
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 31
    • 33750506733 scopus 로고    scopus 로고
    • Aziridines are preferentially ring-opened by soft, heteroatom-based nucleophiles (Ref. 21). For the most recent examples, see:
    • Aziridines are preferentially ring-opened by soft, heteroatom-based nucleophiles (Ref. 21). For the most recent examples, see:. Wu J., Sun X., and Sun W. Org. Biomol. Chem. 4 (2006) 4231-4235
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 4231-4235
    • Wu, J.1    Sun, X.2    Sun, W.3
  • 39
    • 4143102531 scopus 로고    scopus 로고
    • For the earlier examples, see: Ref. 21
    • Ding C.-H., Dai L.-X., and Hou X.-L. Synlett (2004) 1691-1694 For the earlier examples, see: Ref. 21
    • (2004) Synlett , pp. 1691-1694
    • Ding, C.-H.1    Dai, L.-X.2    Hou, X.-L.3
  • 40
    • 34249997960 scopus 로고    scopus 로고
    • note
    • 22d (3.5-10.1 equiv), Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1996, 333-335 (2-3 equiv). These methods are economically viable only if a carbon nucleophile is inexpensive and readily available.
  • 41
    • 34249999902 scopus 로고    scopus 로고
    • note
    • 27a).
  • 45
    • 34250003336 scopus 로고    scopus 로고
    • note
    • Solubilization of copper salts effected by anhydrous lithium salts (LiCl or LiBr) also led to inactive copper species.
  • 46
    • 34249983304 scopus 로고    scopus 로고
    • note
    • Compounds (S,S)-12 and (S,R)-12 are orthogonally protected diamines 1 and 2, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.