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Organic Letters
Volumn 11, Issue 1, 2009, Pages 165-168
Homologation of boronic esters with Lithiated epoxides for the stereocontrolled synthesis of 1,2-And 1,3-diols and 1,2,4-triols
Author keywords

[No Author keywords available]
Indexed keywords

ALCOHOL DERIVATIVE; BORONIC ACID DERIVATIVE; EPOXIDE; ESTER; LITHIUM; ORGANOMETALLIC COMPOUND;
EID: 59649103093     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802651b     Document Type: Article
Times cited : (66)
References (45)
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    • (1996) Chem. Rev , vol.96 , pp. 3303-3326
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  • 15
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    • See also: Blakemore, P. R.;
    • See also: Blakemore, P. R.;
  • 16
    • 33947430499 scopus 로고    scopus 로고
    • Blakemore, P. R
    • Burge, M. S. J. Am. Chem. Soc. 2007, 129, 3068-3069. Blakemore, P. R.;
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 3068-3069
    • Burge, M.S.1
  • 21
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    • 2Zn also furnish alkenes. See: (a) Ukaji, Y.; Fujisawa, T. Tetrahedron Lett. 1988, 29, 5165-5168.
    • 2Zn also furnish alkenes. See: (a) Ukaji, Y.; Fujisawa, T. Tetrahedron Lett. 1988, 29, 5165-5168.
  • 30
    • 64649084003 scopus 로고    scopus 로고
    • In situ trapping is necessary since the lithiated epoxide is thermally unstable. See ref 8
    • In situ trapping is necessary since the lithiated epoxide is thermally unstable. See ref 8.
  • 31
    • 64649083750 scopus 로고    scopus 로고
    • General Procedure for the Homologation of Boronate with Epoxides Leading to Diols 3. A 10-mL Schlenk tube was charged with the corresponding epoxide (0.50 mmol) and boronate (1.00 mmol, 1.00 M in THF, The resulting solution was thereafter cooled to -30 °C followed by dropwise addition of freshly prepared lithium 2, 2, 6, 6-tetramethylpiperidide (1.00 mmol, The reaction mixture was then stirred for 2 h at -30 °C at which time the reaction flask was transferred to an ice bath and NaOH (1.0 mL, 2.0 M) and H2O2 (0.50 mL,>30% w/v) were added. The reaction mixture was stirred an additional 2 h at 4 °C and was then diluted with H 2O (5 mL) and extracted with DCM 4×7 mL, The combined organic layer was dried over magnesium sulphate. The organic solvents were then removed, and the crude product was subjected to silica gel flash chromatography
    • 2O (5 mL) and extracted with DCM (4×7 mL). The combined organic layer was dried over magnesium sulphate. The organic solvents were then removed, and the crude product was subjected to silica gel flash chromatography.
  • 34
    • 0001175929 scopus 로고    scopus 로고
    • Sadhu, K. M.; Matteson, D. S. Organomet al.lics 1985, 4, 1687-1689.
    • (a) Sadhu, K. M.; Matteson, D. S. Organomet al.lics 1985, 4, 1687-1689.
  • 41
    • 64649106018 scopus 로고    scopus 로고
    • These conditions could not be applied to entry 5, Table 1 in order to limit the extent of elimination since the procedure involves deprotonation of the epoxide in the presence of the boronic ester. If TESOTf was also present, it would simply trap the lithiated epoxide as it was being generated.
    • These conditions could not be applied to entry 5, Table 1 in order to limit the extent of elimination since the procedure involves deprotonation of the epoxide in the presence of the boronic ester. If TESOTf was also present, it would simply trap the lithiated epoxide as it was being generated.
  • 42
    • 64649097293 scopus 로고    scopus 로고
    • In the absence of TESOTf, elimination dominated even at low temperature
    • In the absence of TESOTf, elimination dominated even at low temperature.
  • 43
    • 64649096140 scopus 로고    scopus 로고
    • General Procedure for the Homologation of Boronates with Styrene Oxide Leading to Compounds 9. A 10-mL Schlenk tube was charged with (R, styrene oxide (46 μL, 0.40 mmol) and TMEDA (180 νL, 1.20 mmol) in 2.75 mL of ether. The resulting solution was thereafter cooled to -115 °C followed by dropwise addition of s-BuLi (1.3 M in hexanes, 370 μL, 0.48 mmol, The resulting mixture was stirred at -115 °C for 10 min. A solution of the corresponding boronic ester (0.50 mmol) in ether (1.25 mL) was then slowly added, and the mixture was then stirred at -110 °C for 10 min. TES-OTf (113 μL, 0.50 mmol) was added, and the resulting mixture was allowed to warm to room temperature. The reaction flask was transferred to an ice bath, and 3 mg of 2, 6-di-tert-butyl-4-methylphenol was added, followed by a mixture of NaOH (1.0 mL, 2.0 M) and H2O2 0.50 mL,>30% w/v, previously degassed under vacuum. The reaction mixture was stirred
    • 2O (5 mL) and extracted with ether (4×7 mL). The organic solvents were then removed, and the crude product was subjected to silica gel flash chromatography.

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