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Volumn , Issue 14, 2007, Pages 2277-2279

Diastereoselective synthesis of 1-aryl-2-amino-cyclopropane carboxylates

Author keywords

Amino cyclopropanes; Cyclopropanation; Diastereoselective; Diazoacetates; Rhodium

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; IMIDE; METHYL 1 ARYL 2 AMINO CYCLOPROPANE CARBOXYLIC ACID DERIVATIVE; N VINYLPHTHALIMIDE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DECOMPOSITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34548748045 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-985587 Document Type: Article

Times cited : (16)

References (19)

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12
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- N-Vinylphthalimide is commercially available and has been used in cyclopropanation of aryldiazomethanes. See: Aggarwal, V. K.; Vicente, J.; Bonnert, R. V. Org. Lett. 2001, 3, 2785.
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- The aryldiazoacetates used in this study were synthesized in high yields according to a literature procedure: Davies, H. M. L, Townsend, R. J. J. Org. Chem. 2001, 66, 6595
- The aryldiazoacetates used in this study were synthesized in high yields according to a literature procedure: Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595.

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15
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- CCDC-286242 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax +44(1223)336033; or deposit@ccdc.cam.ac.uk].
- CCDC-286242 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax +44(1223)336033; or deposit@ccdc.cam.ac.uk].

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18
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- Enantiomeric excess measured by chiral HPLC. Absolute stereochemistry not determined
- Enantiomeric excess measured by chiral HPLC. Absolute stereochemistry not determined.

19
- 34548743442
- General Experimental Procedure To a solution of Rh 2(OAc)4 (0.03 mmol) and N-vinylphthalimide (3.3 mmol) in CH2Cl2 (5 mL) at r.t, was added dropwise over 1 h, a solution of aryldiazoacetate (3.0 mmol) in CH2Cl2 (10 mL, The resulting solution was stirred for an additional 15 min before the solvent was removed in vacuo. Flash chromatography of the crude product [silica gel. eluting with hexane-Et2O (1:3, yielded the desired cyclopropane 2 as a white solid. All cyclopropanes 2a-i were characterized by 1H NMR and 13C NMR spectroscopy, MS, HRMS and melting points. Spectroscopic data for 2a: 1H NMR (300 MHz, CDCl 3, δ, 2.14 (dd, 1 H, J, 9.0, 6.3 Hz, CH2, 3.15 (t, 1 H, J, 6.1 Hz, CH2, 3.69 (s, 3 H, OCH 3, 3.84 (dd, 1 H, J, 9.0,5.9 Hz, CH, 7.17 (m, 5 H, 7.61 m, 4 H
- 3.

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