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Synlett

Volumn , Issue 13, 2008, Pages 2046-2050

Reaction of a polycyclic diketone with lithiated methoxyallene: Synthesis of new functionalized cage compounds

(4) Zimmer, Reinhold a Taszarek, Maurice a Schefzig, Luise a Reissig, Hans Ulrich a

a FREIE UNIVERSITÄT BERLIN (Germany)

Author keywords

Cage molecules; Crown ether; Epoxidation; Methoxyallene; Ozonolysis

Indexed keywords

ALLENE DERIVATIVE; DIKETONE;

ARTICLE; CHEMICAL ANALYSIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 49649097764 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077975 Document Type: Article

Times cited : (10)

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62
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- Bisallenyl Adduct 4 Methoxyallene (4.20 g, 60.0 mmol) was dissolved in dry THF (35 mL) and treated with n-BuLi (16.0 mL, 40.0 mmol, 2.5 M in hexanes) at -40 °C under argon atmosphere. After 5 min the solution of 2 was cooled to -78 °C and diketone 1 (0.522 g, 3.00 mmol, dissolved in 5 mL of THF) was added within 5 min. The reaction mixture was stirred for 2 h at -78 °C and quenched with sat. aq NH 4Cl solution (25 mL, Warmup to r.t. was followed by extraction with Et2O (3 × 30 mL) and drying (Na2SO4, Purification of the crude product by recrystallization (hexane-Et2O) provided 4 (0.678 g, 74, as a beige-colored solid, mp 148-150 °C. 1H NMR (250 MHz, CDCl3, δ, 1.03, 1.54 (AB system, JAB, 10.5 Hz, 2 H, CH2, 2.25-2.46,2.61-2.73 (2 m, 4 H each, 8 CH, 3.43 (s, 6 H, OMe, 5.46 (s, 2 H, OH, 5.48 s, 4 H, CH 2
- 4 (314.4): C, 72.59; H, 7.05. Found: C, 71.81; H, 6.97.

63
- 49649098035
- Compound 5 To a solution of 4 (0.205 g, 0.655 mmol) in CH2Cl2 (13 mL) mesyl chloride (0.082 g, 0.723 mmol, dissolved in 2 mL of CH2Cl2) and Et3N (0.658 g, 6.55 mmol) were added at O °C. The solution was warmed up to r.t. and stirred for additional 2.5h. Then, sat. aq NH4Cl solution (5 mL) was added and the phases were separated. The organic phase was successively washed with H2O (3 × 5 mL) and brine (1 × 5 mL) and dried (Na2SO4, Purification of the crude product by chromatography on alumina (hexane-EtOAc, 4:1) provided 5 (0.186 g, 96, as an orange resin. 1H NMR (250 MHz, CDCl3, δ, 1.55, 1.92 (AB system, JAB, 10.5 Hz, 2 H, CH2, 2.43, 2.65, 2.86, 2.93 (4 br s, 2 H each, 8 CH, 3.46 (s, 6 H, OMe, 5.51 (s, 4 H, CH2, 13C NMR 62.9 MHz, CDCl3, δ, 198.7
- 3: 296.1412; found: 296.1442.

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66
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- The diester 7 was recently obtained by a one-pot reaction of 1 with dimethoxycarbene in moist toluene in 19% yield, see: Romański, J.; Mlostón, G.; Heimgartner, H. Helv. Chim. Acta 2007, 90, 1279.
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67
- 49649109624
- Ozonolysis of Bisallenyl-Substituted Compound 5 To a solution of 5 (0.37 g, 1.25 mmol) in MeOH (30 mL) argon was bubbled for 5 min with cooling to -78 °C. Then, the solution was treated with ozone until the solution remained blue for 20 min, followed by oxygen for 5 min. The reaction mixture was allowed to warm to r.t. within 1h and the solvent was evaporated in vacuo. Purification of the crude product by chromatography (alumina, hexane-EtOAc, 4:1,1:1 to 0:1) afforded diester 7 (0.080g, 23, as colorless crystals and methyl ketone 8 (0.033 g, 10, as a pale yellow oil. Diester 7: mp 134-136 °C. 1H NMR (250 MHz, CDCl 3, δ, 1.66, 2.04 (AB system, JAB, 11 Hz, 2 H, CH2, 2.60-2.88,3.00-3.15 (2 m, 4 H each, 8 CH, 3.80(s, 6 H, CO2Me, 13C NMR (62.9 MHz, CDCl3, δ, 43.2 (t, CH2, 42.1, 45.2, 49.2, 58.6 (4 d, CH, 52.2 (q, OMe, 94.7 s, C-3
- +, 154 (17), 137 (25), 136 (19), 105 (21), 81 (26), 69 (34), 55 (49), 43 (47).

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- and references therein, For a mechanistic discussion of the ozonolysis of allenes, see
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70
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- -and conversion of the carbonyl group into an acetal moiety by the solvent methanol may lead to this side product (Scheme 2). (Chemical Equation Presented) Scheme 2
- -and conversion of the carbonyl group into an acetal moiety by the solvent methanol may lead to this side product (Scheme 2). (Chemical Equation Presented) Scheme 2

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- Stock, H.T.¹ Kellogg, R.M.²

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- It should be noted that the yield of 11 may be enhanced by a template-directed reaction of 9 and 10 (e.g., by the use of a Cs salt). See also ref. 15.
- It should be noted that the yield of 11 may be enhanced by a template-directed reaction of 9 and 10 (e.g., by the use of a Cs salt). See also ref. 15.

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- Reaction of 9 and 10 To a suspension of NaH (4 mg, 0.16 mmol) in THF (1 mL) were added a solution of 9 (18 mg, 0.08 mmol, dissolved in 5 mL of THF) and a solution of 10 (43 mg, 0.08 mmol, dissolved in 10 mL of THF) over a period of 30 min. The reaction mixture was refluxed for 84 h and after cooling to r.t. H2O (10 mL) was added, and the phases were separated. The aqueous phase was extracted with CH2Cl2 (3 × 20 mL) and the combined organic phases were dried with MgSO4. Purification of the crude product by chromatography (SiO2, hexane-EtOAc, 4:1, 1:1, then 1:3) gave product 11 (3 mg, 7, as a pale yellow resin and starting material 10 (5 mg, 12, Product 11: [α]D, 6.7 (c 0.08, CHCl3, 1H NMR (250 MHz, CDCl3, δ, 0.83, 0.87 (2 d, J, 10 Hz, 1 H each, CH2, 0.99-1.80 (m, 8 H, CH, 3.25-4.55 m, 12 H, OCH
- 5: 558.24060; found: 558.24255.

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- For chiral recognition of racemic primary amines by BINOL-containing crown ethers, see: a
- For chiral recognition of racemic primary amines by BINOL-containing crown ethers, see: (a) Kyba, E. P.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 2692.
- (1973) J. Am. Chem. Soc , vol.95 , pp. 2692
- Kyba, E.P.¹ Koga, K.² Sousa, L.R.³ Siegel, M.G.⁴ Cram, D.J.⁵

77
- 0001050547
- (b) Cram, D. J. Science 1974,183, 803.
- (1974) Science , vol.183 , pp. 803
- Cram, D.J.¹

78
- 0001615838
- (c) Yamamoto, K.; Yunioka, H.; Okamoto, Y.; Chikamatsu, H. J. Chem. Soc., Chem. Commun. 1987, 168.
- (1987) J. Chem. Soc., Chem. Commun , pp. 168
- Yamamoto, K.¹ Yunioka, H.² Okamoto, Y.³ Chikamatsu, H.⁴

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- Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992,114, 1511; see also refs. 15 and 16.
- (d) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992,114, 1511; see also refs. 15 and 16.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.