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Volumn 45, Issue 5, 2004, Pages 1023-1026

One-pot synthesis of α-diazo-β-hydroxyesters under phase-transfer catalysis and application to the catalytic asymmetric aldol reaction

Author keywords

Aldol reaction; Ammonium salt; Asymmetric synthesis; Diazoester; Phase transfer

Indexed keywords

ALDEHYDE DERIVATIVE; CHLORIDE; ESTER DERIVATIVE; TOLUENESULFONYL CHLORIDE; UNCLASSIFIED DRUG;

EID: 0347022323     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.083     Document Type: Article
Times cited : (41)

References (26)
  • 2
    • 0003795884 scopus 로고    scopus 로고
    • Y. Sasson, & R. Neumann. London: Blackie A&M
    • Sasson Y., Neumann R. Handbook of Phase-Transfer Catalysis. 1997;Blackie A&M, London.
    • (1997) Handbook of Phase-Transfer Catalysis
  • 5
    • 0008247380 scopus 로고
    • For aldol reactions using α-diazo carbonyl compounds and their derivatives, see:
    • For aldol reactions using α-diazo carbonyl compounds and their derivatives, see: Bukoth T.L. Tetrahedron Lett. 1969;5049.
    • (1969) Tetrahedron Lett. , pp. 5049
    • Bukoth, T.L.1
  • 11
    • 85030934271 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo. Subsequent flash column chromatography (hexane-AcOEt 10:1) gave the desired product 4a as a yellow oil (190 mg. 0.86 mmol, 82%).
  • 12
    • 0141786837 scopus 로고    scopus 로고
    • Quite recently, a successful catalytic asymmetric aldol reaction of diazoester using chiral Zr complex has been reported. See:
    • Quite recently, a successful catalytic asymmetric aldol reaction of diazoester using chiral Zr complex has been reported. See: Yao W., Wang J. Org. Lett. 5:2003;1527.
    • (2003) Org. Lett. , vol.5 , pp. 1527
    • Yao, W.1    Wang, J.2
  • 13
    • 0001667250 scopus 로고    scopus 로고
    • For successful results using OH free salts with an anthracene unit derived from cinchona alkaloids, see:
    • For successful results using OH free salts with an anthracene unit derived from cinchona alkaloids, see: Zhang F.-Y., Corey E.J. Org. Lett. 3:2001;639.
    • (2001) Org. Lett. , vol.3 , pp. 639
    • Zhang, F.-Y.1    Corey, E.J.2
  • 15
    • 0000234063 scopus 로고    scopus 로고
    • For successful examples using O-protected PTC, see:
    • For successful examples using O-protected PTC, see: Corey E.J., Xu F., Noe M.C. J. Am. Chem. Soc. 119:1997;12414.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12414
    • Corey, E.J.1    Xu, F.2    Noe, M.C.3
  • 22
    • 85030926030 scopus 로고    scopus 로고
    • note
    • D and mp of quaternary salt as described above, and ee of 3a.
  • 23
    • 85030927988 scopus 로고    scopus 로고
    • 3 benzyl derivatives resulted in much lower ee
    • 3 benzyl derivatives resulted in much lower ee.
  • 24
    • 85030925657 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo. Following flash column chromatography (hexane-AcOEt 15:1) gave the desired aldol product 3a as a yellow oil (79 mg, 0.31 mmol, 91%).
  • 26
    • 0033553382 scopus 로고    scopus 로고
    • For asymmetric induction via kinetic resolution and retroaldol reaction under PTC conditions, see:
    • For asymmetric induction via kinetic resolution and retroaldol reaction under PTC conditions, see: Arai S., Shirai Y., Ishida T., Shioiri T. Tetrahedron. 55:1999;6375.
    • (1999) Tetrahedron , vol.55 , pp. 6375
    • Arai, S.1    Shirai, Y.2    Ishida, T.3    Shioiri, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.