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Volumn , Issue 4, 2008, Pages 621-623

An efficient procedure for the 1,3-transposition of allylic alcohols based on lithium naphthalenide induced reductive elimination of epoxy mesylates

Author keywords

1,3 transposition; Allylic alcohols; Epoxy mesylates; Lithium naphthalenide; Reductive elimination

Indexed keywords

ALLYL COMPOUND; EPOXIDE; LITHIUM DERIVATIVE; MESYLIC ACID DERIVATIVE;

EID: 40949111966     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032092     Document Type: Article
Times cited : (16)

References (34)
  • 13
    • 0027395394 scopus 로고
    • For some examples of using LN as a reducing reagent, see: a
    • For some examples of using LN as a reducing reagent, see: (a) Guijarro, A.; Roman, D. J.; Yus, M. Tetrahedron 1993, 49, 469.
    • (1993) Tetrahedron , vol.49 , pp. 469
    • Guijarro, A.1    Roman, D.J.2    Yus, M.3
  • 20
    • 40949112418 scopus 로고    scopus 로고
    • 1H NMR spectrum.
    • 1H NMR spectrum.
  • 21
    • 40949153535 scopus 로고    scopus 로고
    • Typical Procedure for the Reductive Elimination of Epoxy Mesylates: A stock solution of LN11 in THF (0.365 M, 20.4 mL, 7.43 mmol) precooled to -25 °C was quickly added by syringe to a solution of 1a (580 mg, 2.48 mmol) in anhyd THF (5 mL) at -25 °C under a nitrogen atmosphere. The resulting dark mixture was stirred at -25 °C for 10 min, then was quenched with H2O (10 mL) and extracted with EtOAc (2 x 20 mL, The combined extracts were washed with sat. aq NaCl (10 mL, dried with Na2SO4 and concentrated. Purification by chromatography on silica gel (hexane; EtOAc-hexane, 1:10) afforded 1,5,5-trimethyl-cyclohex-2-enol (2a) as a viscous oil (291 mg, 84, IR (KBr, 3490, 1675 cm-1. 1NMR (400 MHz, CDCl3, δ, 5.66 (dt, J, 1.5, 9.9 Hz, 1 H, 5.69 (d, J, 9.9 Hz, 1 H, 1.79 (dd, J, 1.5, 15.1 Hz, 1 H, 1.77 (dd, J, 1.5, 15.1 Hz, 1 H, 1.64 d, J
    • 16O: 140.1201; found: 140.1204.
  • 22
    • 0031592554 scopus 로고    scopus 로고
    • For preparing a stock Solution of LN, see
    • For preparing a stock Solution of LN, see: Liu, H. J.; Yip, J.; Shia, K. S. Tetrahedron Lett. 1997, 38, 2253.
    • (1997) Tetrahedron Lett , vol.38 , pp. 2253
    • Liu, H.J.1    Yip, J.2    Shia, K.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.