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Volumn 74, Issue 3, 2009, Pages 1200-1204

Remote stereocontrol mediated by a sulfinyl group: Synthesis of allylic alcohols via chemoselective and diastereoselective reduction of γ-methylene δ-ketosulfoxides

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOLS; CHELATING AGENTS; CHEMO SELECTIVITIES; CHEMO-SELECTIVE; DIASTEREO SELECTIVITIES; DIASTEREOSELECTIVE REDUCTIONS; ENANTIOMERIC PURITIES; GEL TREATMENTS; REDUCTION PRODUCTS; REMOTE CONTROLLERS; REMOTE STEREOCONTROL; SULFINYL GROUPS; ULTRASOUND IRRADIATIONS; UNSATURATED KETONES;

EID: 64549110313     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802378s     Document Type: Article
Times cited : (30)

References (60)
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    • (a) Gais, H.-J. In Asymmetric Synthesis; Christmann, M., Braese, S., Eds.; Wiley-VCH: Weinheim, 2007, p 84.
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    • Gais, H.-J.1
  • 43
    • 64549110887 scopus 로고    scopus 로고
    • This high affinity of the sulfinyl oxygen for different Lewis acids had been repeatedly evidenced in many 1,2-and 1,3-asymmetric induction processes. See: (a) Carreno,M.C. Chem. Rev. 1995, 95, 1717
    • This high affinity of the sulfinyl oxygen for different Lewis acids had been repeatedly evidenced in many 1,2-and 1,3-asymmetric induction processes. See: (a) Carreno,M.C. Chem. Rev. 1995, 95, 1717.
  • 47
    • 24744457522 scopus 로고    scopus 로고
    • For the use of ultrasound in synthetic organic chemistry, see
    • (a) Peng, Y.; Dou, R.; Song, G.; Jiang, J. Synlett 2005, 14, 2245. For the use of ultrasound in synthetic organic chemistry, see:
    • (2005) Synlett , vol.14 , pp. 2245
    • Peng, Y.1    Dou, R.2    Song, G.3    Jiang, J.4
  • 50
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    • 2CO.
    • 2CO.
  • 52
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    • It is worth of mentioning the appearance of the 1,4-adduct of methanol in the reaction mixture when the chelation time of the α-methyleneketone 1a with the Lewis acid in methanol solution was increased up to 40 min prior to the addition of the reducing agent.
    • It is worth of mentioning the appearance of the 1,4-adduct of methanol in the reaction mixture when the chelation time of the α-methyleneketone 1a with the Lewis acid in methanol solution was increased up to 40 min prior to the addition of the reducing agent.
  • 58
    • 64549143765 scopus 로고    scopus 로고
    • The approach of the borohydride to the opposite face, which would yield compounds 6(a-d)B, is hindered by the substituents at Yb.
    • The approach of the borohydride to the opposite face, which would yield compounds 6(a-d)B, is hindered by the substituents at Yb.
  • 59
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    • The Posner model has been invoked to explain the stereoselectivity of the reduction of α-alkylidene-β-ketosulfoxides: (a) Posner, G. H, Mallamo, J. P, Hulce, M, Frye, L. L. J. Am. Chem. Soc. 1982, 104, 4180
    • The Posner model has been invoked to explain the stereoselectivity of the reduction of α-alkylidene-β-ketosulfoxides: (a) Posner, G. H.; Mallamo, J. P.; Hulce, M.; Frye, L. L. J. Am. Chem. Soc. 1982, 104, 4180.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.