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Synlett

Volumn , Issue 4, 2007, Pages 547-550

Catalytic asymmetric alkylation of α-cyanocarboxylates using a phase-transfer catalyst

(3) Nagata, Kazuhiro a Sano, Daisuke a Itoh, Takashi a

a SHOWA UNIVERSITY (Japan)

Author keywords

Alkylation; Asymmetric synthesis; Halides; Indoles; Phase transfer catalysis

Indexed keywords

ALPHA CYANOCARBOXYLATE DERIVATIVE; CARBON; CARBOXYLIC ACID DERIVATIVE; HALIDE; INDOLE DERIVATIVE; OXINDOLE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BENZYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HYDROLYSIS; SYNTHESIS;

EID: 33947330914 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967963 Document Type: Article

Times cited : (20)

References (37)

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19
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- The yield and ee using other commercially available chiral PTC's under the same reaction conditions, were as follows: N-benzylcinchoninium chloride (trace, 19% ee), N-benzylcinchonidinium chloride (yield: 13%, 17% ee), N-[4-(trifluoromethyl)benzyl]cinchonidinium bromide (yield: 10%, 28% ee), N-benzylquininium chloride (yield: 20%, 19% ee), N-benzylquinidinium chloride (yield: 19%, 3% ee), N-(9- anthracenylmethyl)cinchonidinium chloride (yield: 10%, 0% ee), TaDiAS-[(4R,5R)-2,2-dipropyl-N,N,N′,N′- tetrakis(4-methylbenzyl)]bis(tetrafluoroborate) (yield: 42%, 4% ee).
- The yield and ee using other commercially available chiral PTC's under the same reaction conditions, were as follows: N-benzylcinchoninium chloride (trace, 19% ee), N-benzylcinchonidinium chloride (yield: 13%, 17% ee), N-[4-(trifluoromethyl)benzyl]cinchonidinium bromide (yield: 10%, 28% ee), N-benzylquininium chloride (yield: 20%, 19% ee), N-benzylquinidinium chloride (yield: 19%, 3% ee), N-(9- anthracenylmethyl)cinchonidinium chloride (yield: 10%, 0% ee), TaDiAS-[(4R,5R)-2,2-dipropyl-N,N,N′,N′- tetrakis(4-methylbenzyl)]bis(tetrafluoroborate) (yield: 42%, 4% ee).

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24
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- General procedure: A solution of tert-butyl 2-cyanopropanoate or tert-butyl 2-cyanopent-4-enoate (0.1 mmol) in Et2O (2.4 mL) was cooled to -60°C. The PTC (1a or 1b, 0.001 mmol, alkyl halide (0.12 mmol) and then CsOH (75 mg, 0.5 mmol) were added to the solution. The reaction mixture was vigorously stirred for the time indicated in Table 2 and then diluted with Et2O. The organic layer was washed with H 2O and brine, dried over MgSO4 and the solvents evaporated. The residue was purified using flash column chromatography on silica gel (EtOAc-hexane) to give the corresponding 2-cyanocarboxylate in the yield indicated, R)-tert-Butyl 2-cyano-2-methyl-3-phenylpropanoate (3c) Colorless oil; [α]D25 -14.7 (c 2.00, CHCl3, 97% ee, 1H NMR (400 MHz, CDCl3, δ, 1.42 (s, 9 H, 1.57 (s, 3 H, 2.98-3.01 d, J, 13.7Hz, 1 H, 3.17-3.21
- 2N: 272.1621; found: 272.1662. The ee was determined by HPLC analysis (Daicel CHIRALCEL OD, 2-propanol-hexane, 1:800). 1-tert-Butyl 4-ethyl 2-cyano-2-prop-2-en-1-ylbutanedioate (9) Colorless oil;

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32
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- Compound 10 was prepared from 2′-bromophenylacetonitrile according to a literature procedure, see: Albarella J. P.; J. Org. Chem.; 1977, 42: 2009
- Compound 10 was prepared from 2′-bromophenylacetonitrile according to a literature procedure, see: Albarella J. P.; J. Org. Chem.; 1977, 42: 2009

33
- 33947310473
- R)-tert-Butyl 2-(2-bromophenyl)-2-cyanopent-4-enoate (11) A solution of 10 (29.6 mg, 0.1 mmol) in toluene (2.4 mL) was cooled to -10°C, and PTC 1b (1.1 mg, 0.001 mmol, allyl iodide (18 μL, 0.2 mmol) and then CsOH (75 mg, 0.5 mmol) were added to the solution. The reaction mixture was stirred vigorously for 1 d and then diluted with H 2O. The mixture was extracted with CH2Cl2 and the combined organic layers were washed with brine and dried over MgSO 4. After the solvent was removed by evaporation, the residue was purified by flash column chromatography on silica gel (EtOAc-hexane, 1:16) to give 11 in quantitative yield; colorless oil; [α]D 25 -9.2 (c 2.00, CHCl3, 93% ee, 1H NMR (400 MHz, CDCl3, δ, 1.48 (s, 9 H, 3.11 (dd, J, 7.6, 14.0 Hz, 1 H, 3.27 (dd, J, 6.8, 14.0 Hz, 1 H, 5.19-5.26 (m, 2 H, 5.78 m, 1 H, 7
- 2NBr: 336.0630; found: 336.0584. The ee was determined by HPLC analysis (Daicel CHIRALCEL OJ-H, 2-propanol-hexane, 1:100).

34
- 33947325203
- This result suggested that the Si:Re selectivity of compounds 2 and 10 in the enolate-forming step was opposite to each other. Mechanistic consideration of the asymmetric induction is now under investigation
- This result suggested that the Si:Re selectivity of compounds 2 and 10 in the enolate-forming step was opposite to each other. Mechanistic consideration of the asymmetric induction is now under investigation.

35
- 33947328892
- R)-N-Benzyl-2-(2-bromophenyl)-2-cyanopent-4-enamide (12) Compound 11 (34 mg, 0.1 mmol) was dissolved in TFA (1.0 mL) and stirred at r.t. for 12 h under an argon atmosphere. The TFA was then removed by evaporation and CH2Cl2 (1.0 mL) was added. The solution was cooled to 0°C and EDC·HCl (38 mg, 0.2 mmol, 1-hydroxy-7- azabenzotriazole (27 mg, 0.2 mmol, and BnNH2 (16 μl, 0.15 mmol) were added. The reaction mixture was stirred overnight at r.t. under an argon atmosphere. After the addition of H2O, the mixture was extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and the solvents removed by evaporation. The residue was purified by flash column chromatography on silica gel (EtOAc-hexane, 1:4) to give compound 12 in 88% yield; mp 124°C (CH2Cl2, α]D25 -21.9 c 3.07, CHCl3, 93% ee
- 2Br: C, 61.80; H, 4.64; N, 7.59. Found: C, 61.78; H, 4.54; N, 7.48. The ee was determined by HPLC analysis (Daicel CHIRALCEL OJ-H, 2-propanol-hexane, 1:20).

36
- 0037871666
- Yamada, K.; Kurokawa, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 6603.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 6603
- Yamada, K.¹ Kurokawa, T.² Tokuyama, H.³ Fukuyama, T.⁴

37
- 33947329523
- R)-1-Benzyl-3-cyano-3-prop-2-en-1-yl)-1,3-dihydroindol-2-one (13) To a solution of compound 12 (44 mg, 0.11 mmol) in DMSO (1.1 mL) were added CuI (42 mg, 0.2 mmol) and CsOAc (106 mg, 0.5 mmol, The mixture was stirred for 10 h at 70 °C under an argon atmosphere. After the addition of Et2O, the organic layer was washed with H2O and brine, and dried over MgSO4 The solvent was removed by evaporation and the residue was purified by flash column chromatography on silica gel (EtOAc-hexane, 1:7) to give compound 13 in quantitative yield; mp 122°C (CH 2Cl2, α]D25 +27.3 (c 5.81, CHCl3, 93% ee, 1H NMR (400 MHz, CDCl3, δ, 2.83 (dd, J, 8.4, 13.6 Hz, 1 H, 3.05 (dd, J, 6.4, 13.2 Hz, 1 H, 4.81 (d, J, 15.6 Hz, 1 H, 5.02 (d, J, 15.6 Hz, 1 H, 5.18-5.22 (m, 2 H, 5.65 (m, 1 H, 6.78 d, J, 7.6 Hz
- 2: C, 79.14; H, 5.59; N, 9.72. Found: C, 79.02; H, 5.52; N, 9.75. The ee was determined by HPLC analysis (Daicel CHIRALCEL IA, 2-propanol-hexane, 1:10).

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