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Volumn 50, Issue 26, 2009, Pages 3645-3647

Unexpected cis selectivity in the Pictet-Spengler reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PHENYL GROUP; TRYPTOPHAN DERIVATIVE;

EID: 65549117573     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.121     Document Type: Article
Times cited : (24)

References (19)
  • 11
    • 0033564999 scopus 로고    scopus 로고
    • 4 (Ref. 1), or using a radical reduction route-for example:
    • 4 (Ref. 1), or using a radical reduction route-for example:. Martin S.F., Chen K.X., and Eary C.T. Org. Lett. 1 (1999) 79
    • (1999) Org. Lett. , vol.1 , pp. 79
    • Martin, S.F.1    Chen, K.X.2    Eary, C.T.3
  • 14
    • 65549118024 scopus 로고    scopus 로고
    • note
    • 2CHO] was diastereomerically pure within the NMR detection limits. Using chiral aldehydes (Z-protected α-aminoaldehydes) with Trp-OMe, cis specific reactions have been reported for matched substrates (Pulka, K.; Kulis, P.; Tymecka, D.; Lukasz, F., Wilczek, M.; Kozminski, W.; Misicka, A. Tetrahedron 2008, 64, 1506. Aqueous Pictet-Spengler reactions show typical cis selectivity of about 4:1, although a 9:1 cis:trans ratio was reported for Trp-OMe with 2-hydroxybenzaldehyde (Saha, B.; Sharma, S.; Sawant, D.; Kundu, B. Tetrahedron Lett. 2007, 48, 1379).
  • 16
    • 65549142340 scopus 로고    scopus 로고
    • note
    • 13C derivative of Trp-OBn.]
  • 18
    • 65549111907 scopus 로고    scopus 로고
    • note
    • +: 333.1604. Found: 333.1617 (100%), 334.1642 (10%).
  • 19
    • 65549151449 scopus 로고    scopus 로고
    • note
    • +: 494.6223. Found: 494.6217 (100%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.