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Volumn 54, Issue 15, 1998, Pages 3833-3850

Synthesis of allenic diols by samarium, diiodide-promoted coupling between alkynyloxiranes and ketones

Author keywords

[No Author keywords available]

Indexed keywords

2,3 PENTADIENE 1,5 DIOL; ETHYLENE OXIDE DERIVATIVE; KETONE; REDUCING AGENT; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

EID: 0032499120     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00110-0     Document Type: Article
Times cited : (17)

References (58)
  • 2
    • 0001367782 scopus 로고
    • L. A. Paquette, Ed.; John Wiley & Sons: New York
    • (b) Molander, G. A. In Organic Reactions, L. A. Paquette, Ed.; John Wiley & Sons: New York, 1994; Vol. 46; pp 211-367.
    • (1994) Organic Reactions , vol.46 , pp. 211-367
    • Molander, G.A.1
  • 35
    • 0010579050 scopus 로고    scopus 로고
    • Formation of the enynes probably takes place by ring-opening of epoxides with iodide anion associated to Sm(III), followed by reduction of the corresponding iodohydrins (i.e. 3d): See ref's 2a, 8a,b
    • 9. Formation of the enynes probably takes place by ring-opening of epoxides with iodide anion associated to Sm(III), followed by reduction of the corresponding iodohydrins (i.e. 3d): See ref's 2a, 8a,b.
  • 41
    • 0025256982 scopus 로고
    • 12. The migration of silyl groups between adjacent hydroxyl groups has been shown to proceed under basic conditions: (a) Mulzer, J.; Schöllhorn, B. Angew. Chem. Int. Ed. Engl. 1990, 29, 431-432.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 431-432
    • Mulzer, J.1    Schöllhorn, B.2
  • 43
    • 33845280764 scopus 로고
    • 13. A related SET from Ti(III) species to epoxides yielding α-alkoxy radicals has been reported: Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561-8562.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 8561-8562
    • Nugent, W.A.1    Rajanbabu, T.V.2
  • 44
    • 0000627957 scopus 로고    scopus 로고
    • and references cited therein
    • 14. See for example: Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429, and references cited therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 7418-7429
    • Molander, G.A.1    Harris, C.R.2
  • 47
    • 0010541299 scopus 로고    scopus 로고
    • 5e,18,19 cycloisomerization of diols 2a, d, j further confirmed these stereochemical assignments. See Ref. 6 and following paper in this issue
    • 5e,18,19 cycloisomerization of diols 2a, d, j further confirmed these stereochemical assignments. See Ref. 6 and following paper in this issue.
  • 51
    • 0010543464 scopus 로고    scopus 로고
    • 5a for the preparation of 1b was modified as follows: THF was used as solvent and n-BuLi at -78°C as base
    • 5a for the preparation of 1b was modified as follows: THF was used as solvent and n-BuLi at -78°C as base.
  • 53
    • 0000910413 scopus 로고
    • Purification by distillation, as reported, resulted in isomerization to oct-2-en-2-yl inflate. Alternatively, flash chromatography in hexanes afforded a 93:7 mixture of oct-1-en-2-yl triflate and its isomeric internal triflate
    • 23. Takai, K.; Sakogawa, K.; Kataoka, Y.; Oshima, K.; Utimoto, K. Org. Synth. 1993, 72, 180-188. Purification by distillation, as reported, resulted in isomerization to oct-2-en-2-yl inflate. Alternatively, flash chromatography in hexanes afforded a 93:7 mixture of oct-1-en-2-yl triflate and its isomeric internal triflate.
    • (1993) Org. Synth. , vol.72 , pp. 180-188
    • Takai, K.1    Sakogawa, K.2    Kataoka, Y.3    Oshima, K.4    Utimoto, K.5
  • 56
    • 0010611975 scopus 로고    scopus 로고
    • note
    • 2, should be kept at about 2-3 mol% as the use of larger excesses in reactions of 1a was observed to lead occasionally to the formation of diene byproducts i and to loss of diastereoselectivity in the formation of diols 2. (formula presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.