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Volumn , Issue 4, 2004, Pages 708-710

Lewis acid-catalysed aza-Diels-Alder versus Mannich reactions of N-diethyl phosphoryl imino dienophiles with oxygenated dienes and application of a chiral Lewis acid

Author keywords

Asymmetric induction; Diels Alder reaction; Heterodienophile; Mannich reaction

Indexed keywords

AMPHOLYTE; DIENESTROL; IMINE; LEWIS ACID; N PHOSPHORYLIMINE; UNCLASSIFIED DRUG; ZINC;

EID: 1642273660     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817742     Document Type: Article
Times cited : (20)

References (35)
  • 2
    • 0035898269 scopus 로고    scopus 로고
    • For recent reviews see: (a) Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099. (b) Jørgensen, K. A. Angew. Chem. Int. Ed, 2000, 39, 3558.
    • (2001) Tetrahedron , vol.57 , pp. 6099
    • Buonora, P.1    Olsen, J.-C.2    Oh, T.3
  • 3
    • 0034675619 scopus 로고    scopus 로고
    • For recent reviews see: (a) Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099. (b) Jørgensen, K. A. Angew. Chem. Int. Ed, 2000, 39, 3558.
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3558
    • Jørgensen, K.A.1
  • 23
    • 1642333679 scopus 로고    scopus 로고
    • note
    • 1% TFA quench followed by silica gel chromatography.
  • 24
    • 1642361338 scopus 로고    scopus 로고
    • note
    • All spectroscopic and analytical properties were consistent with the structures assigned.
  • 25
    • 1642325596 scopus 로고    scopus 로고
    • note
    • Developed for the purpose of high throughput screening avoiding an aqueous work up.
  • 26
    • 1642345102 scopus 로고    scopus 로고
    • note
    • The crystals of 12b repeatedly cracked on cooling at about 125 K, which indicated a phase transition at this temperature hence the X-ray data were finally collected at 200 K. The molecule 12b in crystal (Figure 1) shows severe disorder of both ethyl-groups and terminal carbonyl group. The molecule has a trans-configuration around C3=C4 double bond, the conformation around P-N bond is characterised by a torsion angle for O1, P1, N1, C1 of -349(3)°. The molecules of 12b in the crystal are linked together by strong hydrogen bonds N-H⋯O = P(x + 1, y z) (N⋯O 2873(3)Å), forming chains parallel to a-axis.
  • 27
    • 0042826637 scopus 로고
    • The zinc-binol complex was prepared in situ from diethyl zinc and dry (S)-binol: (a) Sakane, S.; Muruoka, K.; Yamamoto, H. Tetrahdron Lett. 1985, 26, 5536. (b) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735. (c) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (1985) Tetrahdron Lett. , vol.26 , pp. 5536
    • Sakane, S.1    Muruoka, K.2    Yamamoto, H.3
  • 28
    • 0012126853 scopus 로고    scopus 로고
    • The zinc-binol complex was prepared in situ from diethyl zinc and dry (S)-binol: (a) Sakane, S.; Muruoka, K.; Yamamoto, H. Tetrahdron Lett. 1985, 26, 5536. (b) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735. (c) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2002) Org. Lett. , vol.4 , pp. 1735
    • Corminboeuf, O.1    Renaud, P.2
  • 29
    • 0013263752 scopus 로고    scopus 로고
    • The zinc-binol complex was prepared in situ from diethyl zinc and dry (S)-binol: (a) Sakane, S.; Muruoka, K.; Yamamoto, H. Tetrahdron Lett. 1985, 26, 5536. (b) Corminboeuf, O.; Renaud, P. Org. Lett. 2002, 4, 1735. (c) Du, H.; Long, J.; Hu, J.; Li, X.; Ding, K. Org. Lett. 2002, 4, 4349.
    • (2002) Org. Lett. , vol.4 , pp. 4349
    • Du, H.1    Long, J.2    Hu, J.3    Li, X.4    Ding, K.5
  • 31
    • 1642294617 scopus 로고    scopus 로고
    • note
    • Asymmetric induction was determined using chiral HPLC on a Chiralpak OD column using i-PrOH-hexane as eluant (96:4) for 3a and 3b; (94:6) for 3c; and (97:3) for 3e.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.