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Volumn 69, Issue 4, 2004, Pages 1262-1269

An Expedient and Practical Method for the Synthesis of A Diverse Series of Cyclopropane α-Amino Acids and Amines

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSTS; ESTERS; OLEFINS; SYNTHESIS (CHEMICAL);

EID: 1242352457     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035596y     Document Type: Article
Times cited : (114)

References (99)
  • 5
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    • For the first isolation see: (a) Burroughs, F. Nature 1957, 179, 360.
    • (1957) Nature , vol.179 , pp. 360
    • Burroughs, F.1
  • 52
    • 1242268794 scopus 로고    scopus 로고
    • note
    • The diastereoselectivities for the two methods vary less than ±2%.
  • 53
    • 1242268793 scopus 로고    scopus 로고
    • note
    • The steric bulk associated with the TBDPS ether appears to be the only factor influencing the reduced chemical yield when using method B. It should be noted that 4-vinylanisole undergoes efficient cyclopropanations using methods A and B (see ref 18).
  • 54
    • 1242336330 scopus 로고    scopus 로고
    • note
    • A variety of additives were tested including toluene, KBr aqueous solutions, molecular sieves, MgO, etc.
  • 55
    • 0141630494 scopus 로고    scopus 로고
    • 2 (0.04 mol %) on a 3.0 g scale. The reaction was heated at 40 °C for 4.5 h, affording 79% isolated yield of cyclopropane 5a in a 92:8 E:Z ratio. For a recent example of reduced catalyst loadings in Rh(II)-catalyzed cyclopropanation reactions see: Davies H. M. L.; Venkataramani, C. Org. Lett. 2003, 5, 1403.
    • (2003) Org. Lett. , vol.5 , pp. 1403
    • Davies, H.M.L.1    Venkataramani, C.2
  • 56
    • 1242268792 scopus 로고    scopus 로고
    • note
    • The benzyl ester was used to reduce the volatility of the corresponding cyclopropyl amine upon reduction.
  • 67
    • 0000357350 scopus 로고
    • It is noteworthy to mention that Stammer et al. have reported the cleavage of the benzyl ester of benzyl (Z)-2-phenyl-1-amino-1-carboxylate in high yields without hydrogenolysis of the cyclopropane ring. See: King, S. W.; Riordan, J. M.; Holt, E. M.; Stammer, C. H. J. Org. Chem. 1982, 47, 3270.
    • (1982) J. Org. Chem. , vol.47 , pp. 3270
    • King, S.W.1    Riordan, J.M.2    Holt, E.M.3    Stammer, C.H.4
  • 75
    • 1242336333 scopus 로고    scopus 로고
    • note
    • There is some erosion of the stereochemical integrity (ca. 10-15%) for styrene-derived cyclopropanes during the course of the nitro reduction. The implicated mechanism pertaining to this surprising observation is under closer examination.
  • 79
    • 25944443366 scopus 로고    scopus 로고
    • May 23
    • (d) Chem. Eng. News 2003, May 23, 31.
    • (2003) Chem. Eng. News , pp. 31
  • 90
    • 1242313826 scopus 로고    scopus 로고
    • note
    • The cis- and trans-isomers of the nitrocyclopropanes can be easily separated by column chromatography. Only the pure transisomers were submitted to the reduction conditions.
  • 91
    • 1242268795 scopus 로고    scopus 로고
    • note
    • A monoaminooxidase inhibitor (MAOI), tranylcypromine (Parnate, Jatrosom N), which is an oral MAOI-type antidepressant, is used to treat major depression in patients who have not responded to other antidepressant therapies.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.