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Volumn 41, Issue 29, 2000, Pages 5561-5565

An efficient and practical preparation of optically active syn-1-vinyl- 2-amino alcohol derivatives by the regio- and diastereoselective addition reaction of (γ-alkoxyallyl)titaniums with chiral imines. Formal synthesis of statine

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ACROLEIN; ALDEHYDE DERIVATIVE; ALPHA METHYLBENZYLAMINE; AMINOALCOHOL; IMINE; PROPYLENE; REAGENT; STATINE; TITANIUM DERIVATIVE; VINYL DERIVATIVE;

EID: 0034662193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00882-0     Document Type: Article
Times cited : (23)

References (29)
  • 5
    • 0001463392 scopus 로고
    • (e) See also Ref 3a
    • (e) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360. See also Ref 3a.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 360
    • Ohfune, Y.1
  • 7
    • 0342908524 scopus 로고
    • The Lewis acid mediated stereoselective addition reactions of γ-alkoxyallylic stannanes with N-acyliminium intermediates providing 1-alkenyl-2-amino alcohol derivatives have been reported: (a)
    • The Lewis acid mediated stereoselective addition reactions of γ-alkoxyallylic stannanes with N-acyliminium intermediates providing 1-alkenyl-2-amino alcohol derivatives have been reported: (a) Yamamoto, Y.; Schmid, M. J. Chem. Soc., Chem. Commun. 1989, 1311.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 1311
    • Yamamoto, Y.1    Schmid, M.2
  • 9
    • 0033603376 scopus 로고    scopus 로고
    • Intramolecular cyclization of chiral imines having γ-alkoxyallylstannyl moiety in the presence of Lewis acid affording α-vinyl-β-amino cyclic ethers has been reported: (c)
    • Intramolecular cyclization of chiral imines having γ-alkoxyallylstannyl moiety in the presence of Lewis acid affording α-vinyl-β-amino cyclic ethers has been reported: (c) Park, J.-Y.; Kadota, I.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4901.
    • (1999) J. Org. Chem. , vol.64 , pp. 4901
    • Park, J.-Y.1    Kadota, I.2    Yamamoto, Y.3
  • 22
    • 0342474231 scopus 로고    scopus 로고
    • 3 (0.5 mL), NaF (1.2 g) and Celite (1.2 g), the mixture was filtered though a pad of Celite. The filtrate was concentrated in vacuo and passed through a short silica gel column to give a mixture of adducts (270 mg) in 69% total yield. Pure 3b (169 mg) was isolated in 55% yield by column chromatography on silica gel
    • 3 (0.5 mL), NaF (1.2 g) and Celite (1.2 g), the mixture was filtered though a pad of Celite. The filtrate was concentrated in vacuo and passed through a short silica gel column to give a mixture of adducts (270 mg) in 69% total yield. Pure 3b (169 mg) was isolated in 55% yield by column chromatography on silica gel.
  • 24
    • 0342474229 scopus 로고    scopus 로고
    • Although it seemed that the reactions using 1 derived from the diethyl acetal would give somewhat better diastereoselectivity as observed in the reaction with 2b, we mainly carried out the reaction of 1 derived from the dibenzyl acetal because the benzyl group of the resulting products 3 can be easily deprotected
    • Although it seemed that the reactions using 1 derived from the diethyl acetal would give somewhat better diastereoselectivity as observed in the reaction with 2b, we mainly carried out the reaction of 1 derived from the dibenzyl acetal because the benzyl group of the resulting products 3 can be easily deprotected.
  • 25
    • 33845279307 scopus 로고
    • Yamamoto, Y.; Nishii, S. J. Org. Chem. 1988, 53, 3597. Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 7873.
    • (1988) J. Org. Chem. , vol.53 , pp. 3597
    • Yamamoto, Y.1    Nishii, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.