SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 3, 2008, Pages 333-338

Parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric active esters

(2) Coulbeck, Elliot a Eames, Jason a

a UNIVERSITY OF HULL (United Kingdom)

Author keywords

Chiral auxiliaries; Chiral resolution; Kinetic resolution; Molecular recognition; Stereoselectivity

Indexed keywords

1 PHENYLETHANOL; ESTER;

ARTICLE; CHEMICAL ANALYSIS; DIASTEREOISOMER; ENANTIOMER; KINETICS; RACEMIC MIXTURE; SYNTHESIS;

EID: 39749117430 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032068 Document Type: Article

Times cited : (11)

References (52)

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26
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- See also ref. 18. (f) For our study, an excess of alcohol rac-16 was used to minimize epimerisation of the product, potential racemisation of the active ester(s) and as a competitive Lewis base.
- (e) See also ref. 18. (f) For our study, an excess of alcohol rac-16 was used to minimize epimerisation of the product, potential racemisation of the active ester(s) and as a competitive Lewis base.

27
- 39749151416
- Alternatively, n-BuLi (in hexanes) and PhLi (in dibutyl ether) could be used but they contained traces of lithium butoxide which can lead to the formation of an inseparable by-product, butyl 2-phenylpropionate (in 16% and 5% yields for n-BuLi and PhLi, respectively, Characterisation data for butyl 2-phenylpropionate; Rf [light PE (40-60°C)-Et 2O, 1:1] 0.80. IR (film, 1674 (C=O) cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.15-7.28 (m, 5 H, 5 x CH, Ph, 3.99 (td, J, 1.5, 6.8 Hz, 2 H, OCH2, 3.63 (q, J, 7.2 Hz, 1 H, CHMe, 1.43-1.52 (m, 2 H, CH2, 1.42 (d, J, 7.2 Hz, 3 H, CHMe, 1.18-1.28 (m, 2 H, CH2, 0.79 (t, J, 7.5 Hz, 3 H, Me, 13C NMR (100 MHz, CDCl3, δ, 174 (C=O, 140.6 (i-C, Ph, 128.4, 127.4, 126.9 (3 x CH, Ph, 64.5 (OCH 2, 45.5 (PhCH, 30.4, 18.9 2 x CH2, 18.4
- 2: 206.1299; found: 206.1301.

28
- 39749144866
- Using racemic lithium 1-(4-methoxyphenyl)ethoxide, epimerisation of esters such as (S,S)-anti-24 and (S,R)-syn-24, has been shown to occur at a significantly faster rate than simple transesterification
- Using racemic lithium 1-(4-methoxyphenyl)ethoxide, epimerisation of esters such as (S,S)-anti-24 and (S,R)-syn-24, has been shown to occur at a significantly faster rate than simple transesterification.

29
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- and references therein
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30
- 39749135906
- 1H NMR (400 MHz) spectroscopy; for rac,anti-17, the methyl doublets appear at δ = 1.43 (d, J = 7.2 Hz, 3 H, MeCH) and 1.42 (d, J = 6.6 Hz, 3 H, MeCH), whereas for rac,syn-17, the methyl doublets appear at δ = 1.41 (d, J = 7.2 Hz, 3 H, MeCH) and 1.35 (d, J = 6.6 Hz, 3 H, MeCH).
- 1H NMR (400 MHz) spectroscopy; for rac,anti-17, the methyl doublets appear at δ = 1.43 (d, J = 7.2 Hz, 3 H, MeCH) and 1.42 (d, J = 6.6 Hz, 3 H, MeCH), whereas for rac,syn-17, the methyl doublets appear at δ = 1.41 (d, J = 7.2 Hz, 3 H, MeCH) and 1.35 (d, J = 6.6 Hz, 3 H, MeCH).

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- Experimental Procedure for 1-Phenylethyl 2- Phenylpropionate, R,R-anti-17] and 1-Phenylethyl 2-(6-Methoxynaphthalen-2-yl) propionate, S,S)-anti-24] Derived from the Parallel Kinetic Resolution of 1-Phenylethanol (rac-16) Using Active Esters (R)-11 and (S)-12: t-BuLi (1.81 mL, 1.7 M in pentane, 3.07 mmol) was added to a stirred solution of 1-phenylethanol (rac-16; 1.25 g, 1.24 mL, 10.25 mmol) in THF at-78°C. A solution of ZnCl2 (3.07 mL, 1 M in Et2O, 3.07 mmol) was added and the resulting solution was stirred for 2 min. An equimolar combination of pentafluorophenyl 2-phenylpropionate, R)-11; 0.16 g, 0.51 mmol] and pentafluorophenyl 2-(6-methoxynaphthalen-2-yl)propionate, S)-12; 0.203 g, 0.51 mmol] in THF (20 mL) was added, and the resulting solution was stirred for 12 h. The reaction was quenched by the addition of sat. aq
- +].

51
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- Fu has reported the use of 2-methyl-2-butanol (t-amyl alcohol) as a solvent within the efficient resolution of 1-phenylethanol using a chiral DMAP equivalent. For additional information, see: Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794.

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