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Synlett 2008(13): 2069-2071  
DOI: 10.1055/s-2008-1077951
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel [3+2] Dipolar Cycloaddition Approach to Hexahydrobenzofuro[3,2-b]pyrroles

Ikyon Kim*, Hee-Kyung Na, Kyung Ran Kim, Sun Gi Kim, Ge Hyeong Lee
Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea
Fax: +82(42)8607160; e-Mail: ikyon@krict.re.kr;
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Publication History

Received 25 April 2008
Publication Date:
15 July 2008 (online)

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Abstract

A highly stereoselective intramolecular 1,3-dipolar cycloaddition reaction of azomethine ylides derived from 2-vinyloxybenzaldehydes proceeded smoothly to allow for a direct access to tricyclic hexahydrobenzofuro[3,2-b]pyrroles in good yields.

Key words

stereoselective synthesis - intramolecular reaction - 1,3-dipolar cycloadditions - azomethine ylides - 2-vinyloxybenzaldehydes - hexahydrobenzofuro[3,2-b]pyrroles

    References and Notes

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3

Spectral Data of 7a
¹H NMR (300 MHz, CDCl3): δ = 7.30-7.21 (m, 2 H), 6.93-6.82 (m, 2 H) 5.67 (dd, J = 7.8, 5.1 Hz, 1 H), 4.59 (d, J = 7.8 Hz, 1 H), 4.22 (q, J = 7.2 Hz, 2 H), 3.94 (d, J = 6.9 Hz, 1 H), 3.76 (s, 3 H), 3.52 (dd, J = 6.9, 5.1 Hz, 1 H), 2.56 (s, 3 H), 1.31 (t, J = 7.2 Hz, 3 H). ¹³C NMR (75 MHz, CDCl3): δ = 170.8, 170.7, 160.1, 130.3, 126.8, 124.9, 121.0, 110.8, 87.8, 69.2, 68.1, 61.1, 54.8, 52.7, 36.3, 14.6. HRMS (EI): m/z calcd for [C16H19NO5]+: 305.1263; found: 305.1265.

4

CCDC 683322 contains the supplementary crystallographic data for compound 7a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

7

Yields were not optimized.