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Synlett
Volumn , Issue 14, 2008, Pages 2183-2187
The conversion of carbonyl compounds into pentadienylamines by a Julia-Kocienski olefination procedure
Author keywords

1,3 pentadienyl amines; 1 phenyl 1H tetrazol 5 yl sulfones; Alkenes; Modified Julia olefination
Indexed keywords

1 PHENYL 1H TETRAZOL 5 YLSULFONE; 1,3 PENTADIENYL AMINE DERIVATIVE; ALKENE DERIVATIVE; AMINE; AZIDE; CARBONYL DERIVATIVE; LITHIUM HEXAMETHYLDISILAZIDE; POTASSIUM HEXAMETHYLDISILAZIDE; SODIUM HEXAMETHYLDISILAZIDE; SULFONE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;
EID: 51149099238     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078011     Document Type: Article
Times cited : (4)
References (31)
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    • For recent applications in natural product synthesis, see: (a) trans-Vaccenic acid: Duffy, P. E.; Quinn, S. M.; Roche, H. M.; Evans, P. Tetrahedron 2006, 62, 4838.
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    • Preparation of tert-Butyl (E)-4-(1- Phenyl-1H-tetrazol-5-ylsulfonyl)but-2-enyl Carbamate (11) To a solution of the sulfide 10 (7 g, 15.6 mmol) and Mo7O 24 (NH4)6·4H2O (5.8 g, 4.7 mmol) in MeOH (130 mL) was added 30% aq H2O2 (48.3 mL, 468 mmol) at r.t. The solution was stirred for 1 h, and then sat. aq Na 2S2O7 solution was added to quench the excess of peroxide. After a stirring for 45 min at r.t, the reaction mixture was extracted with EtOAc (3 x 100 mL, dried (NaSO4, and concentrated in vacuo; purification by silica flash column chromatography (PE-EtOAc, 1:1) gave the title sulfone 11 (5.6 g, 95, as a white solid, mp 86°C; Rf, 0.56 (PE-EtOAc, 1:1, 1H NMR (400 MHz, CDCl3, δ, 1.43 (s, 9 H, t-Bu, 3.77 m, 2 H, CH 2-1
    • +]: 380.13925; found (CI): 380.1392 (0.1 ppm error).
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    • 10,11 In the present study, it would appear that LiHMDS preferentially generates syn-β- alkoxysulfones resulting in a predominance of the E,Z-adducts. The reasons for this unexpected switch are not fully understood at the present time but further studies are in progress to shed light on this interesting observation.
    • 10,11 In the present study, it would appear that LiHMDS preferentially generates syn-β- alkoxysulfones resulting in a predominance of the E,Z-adducts. The reasons for this unexpected switch are not fully understood at the present time but further studies are in progress to shed light on this interesting observation.
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    • Preparation of 1-[N-(tert-Butoxycarbonyl)amino]-5-phenylpenta-2,4-diene (12) To as stirred solution of PT-sulfone 11 (45 mg, 0.12 mmol, 1.2 equiv) in THF (1.4 mL) was added LiHMDS (0.26 mL 1.0 M in THF, 0.26 mmol, 2.55 equiv, or KHMDS (0.52 mL, 0.5 M in toluene, 0.26 mmol, 2.55 equiv, at -78°C. In the KHMDS case, 18-crown-6 (34 mg, 0.13 mmol, 1.2 equiv) was also present at the outset. After 1.5 h at the same temperature, the orange mixture was added to benzaldehyde (10.6 mg, 0.1 mmol, 1.0 equiv) in THF (0.9 mL) at -78°C via cannula. The mixture was stirred at -78° for 1.5 h and then for 1 h at r.t. After quenching with brine (3 mL) and stirring at r.t. for 10 min, the aqueous layer was extracted with EtOAc 3 x 8 mL, The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification was performed via flash chromatography on SiO2 using mixtures of PE and EtOAc as eluent to afford th
    • +: 282.1470; found: 282.1465 (3.5 ppm error)].
  • 31
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    • All novel compounds were fully characterised (sometimes as E,E/E,Z mixtures) including confirmation by high-field NMR and HRMS.
    • All novel compounds were fully characterised (sometimes as E,E/E,Z mixtures) including confirmation by high-field NMR and HRMS.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.