Transfer of alk-1-enyl group from boron to tin: A highly stereoselective synthesis of (E)-alk-1-enyltributylstannanes

Synlett

Volumn , Issue 18, 2009, Pages 2945-2948

  Hoshi, Masayuki ^a   Hayatsu, Takaki ^a   Okimoto, Mitsuhiro ^a   Kodama, Satoshi ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

(E) alk 1 enyldicyclohexylborane; (E) alk 1 enyltributylstannane; Halodestannylation; Transfer; Tributyltin methoxide

Indexed keywords

ALK 1 ENYL; ALK 1 ENYLDICYCLOHEXYLBORANE; ALK 1 ENYLTRIBUTYLSTANNANE; ALKENE DERIVATIVE; BORANE DERIVATIVE; BORON; GALVINOXYL; TIN; TIN DERIVATIVE; TRIBUTYLTIN METHOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HALODESTANNYLATION; ISOMERIZATION; ONE POT SYNTHESIS; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 72049105582     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218009     Document Type: Article

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41. The 1H NMR spectrum of (E)-1-iodohex-1-ene (4a) shows the alkenyl protons at d = 5.97 (dt, J = 14.1, 1.0 Hz) and 6.51 (dt, J = 14.1, 7.3 Hz) ppm.
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43. To a solution of BH3-SMe2 (1 mmol) in THF (3 mL) was added cyclohexene (0.164 g, 2 mmol) dropwise at 0 °C under argon, and the mixture was stirred for 2 h at this temperature to form a white suspension of dicyclohexylborane in THF. To this suspension was added hex-1-yne (0.082 g, 1 mmol) dropwise at 0 °C, and the mixture was stirred for 2 h at this temperature to produce a clear solution of (E)-hex-1-enyldicyclohexylborane (1a) in THF. To this solution was added galvinoxyl (0.004 g, 0.01 mmol) under a flow of argon, followed by dropwise addition of tributyltin methoxide (0.321 g, 1 mmol) at 0 °C. The resulting mixture was allowed to warm to r.t. and stirred for 1 h to generate (E)-hex-1-enyltributylstannane (2a). The solution of 2a, thus prepared, was cooled to -15 °C, and a solution of I2 (0.279 g, 1.1 mmol) in THF (1 mL) was added dropwise. The resulting mixture was allowed to warm to 0 °C and stirred for 0.5 h. The reaction mixture was treated with aq Na2O3S2 to remove excess I2, and then oxidized by the successive addition of 3 M NaOH (1 mL) and 30% H2O2 (0.5 mL) at 0 °C. After being stirred for 1 h at this temperature, the mixture was extracted three times with Et2O. The combined extracts were washed with brine and a 10% aq solution of KF, dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel, with pentane as eluent, to give (E)-1-iodohex-1-ene (4a, 0.151 g, 72%).
44. (E)-Oct-1-enyltributylstannane (2c) was prepared in the same manner as described in ref. 43 but using oct-1-yne (0.110 g, 1 mmol) instead of hex-1-yne. To the solution of 2c in THF was added a solution of pyridinium tribromide (0.384 g, 1.2 mmol) in THF (2 mL) dropwise at -15 °C, and the mixture was allowed to warm to 0 °C and stirred for 0.5 h. The workup procedure was the same as described in ref. 43, except for washing with aq Na2O3S2. Elution with pentane gave (E)-1-bromooct-1-ene (6c, 0.134 g, 70%). The 1H NMR spectrum of 6c shows the alkenyl protons at d = 6.01 (d, J = 13.4 Hz) and 6.15 (dt, J = 13.4, 6.4 Hz) ppm.