Organocatalytic Domino Double
Michael Reaction of Ethyl (E)-7-Oxohept-2-enoate
and α,β-Unsaturated Aldehydes: Efficient Asymmetric
Synthesis of Cyclohexanes with Four Contiguous Stereocenters

Bor-Cherng Hong; Amit A. Sadani; Roshan Y. Nimje; Nitin S. Dange; Gene-Hsiang Lee

doi:10.1055/s-0030-1260469

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Synthesis 2011(12): 1887-1895
DOI: 10.1055/s-0030-1260469

PAPER

Organocatalytic Domino Double Michael Reaction of Ethyl (E)-7-Oxohept-2-enoate and α,β-Unsaturated Aldehydes: Efficient Asymmetric Synthesis of Cyclohexanes with Four Contiguous Stereocenters

Bor-Cherng Hong*^a, Amit A. Sadani^a, Roshan Y. Nimje^a, Nitin S. Dange^a, Gene-Hsiang Lee^b
^a Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, R.O.C.
Fax: +886(5)2721040; e-Mail: chebch@ccu.edu.tw;
^b Instrumentation Center, National Taiwan University, Taipei, 106, Taiwan, R.O.C.

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Publication History

Received 14 March 2011
Publication Date:
16 May 2011 (online)

Abstract
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Abstract

Organocatalytic domino double Michael reactions of ethyl (E)-7-oxohept-2-enoate and α,β-unsaturated aldehydes provided ethyl 2-(2,4-diformyl-3-phenylcyclohexyl)acetate with excellent diastereoselectivities (>20:1 dr) and enantioselectivities (>99% ee). The adducts were further transformed to octahydro-3H-2-benzopyran-3-ones, octahydroisoquinolin-3(2H)-ones, and decahydro-5H-oxazolo[2,3-a]isoquinolin-5-ones.

Key words

Michael addition - aldehydes - organocatalysis - aldol reaction - quinolines

Supporting Information

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The reaction with 1 equiv of dl-Ser-OMeHCl for 8 h resulted in ˜50% conversion of 3a.

17

CCDC-815738 contains the supplementary crystallographic data for (-)-3e, radiation type: CuKα. CCDC-815739 contains the supplementary crystallographic data for (-)-3e, radiation type: MoKα. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

Supplementary Material

Supporting Information