A novel catalytic enantioselective tandem transetherification–intramolecular hetero Diels–Alder reaction of methyl (E)-4-methoxy-2-oxo-3-butenoate with δ,ε-unsaturated alcohols | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

5695347

Reference Type

Journal Article

Title

A novel catalytic enantioselective tandem transetherification–intramolecular hetero Diels–Alder reaction of methyl (E)-4-methoxy-2-oxo-3-butenoate with δ,ε-unsaturated alcohols

Author(s)

Wada, E; Koga, H; Kumaran, G

Year

2002

Is Peer Reviewed?

Journal

Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581

Volume

Issue

Page Numbers

9397-9400

DOI

10.1016/S0040-4039(02)02320-1

Web of Science Id

WOS:000179537900027

URL

http://www.sciencedirect.com/science/article/pii/S0040403902023201
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Abstract

A novel asymmetric tandem transetherification–intramolecular hetero Diels–Alder reaction of methyl (E)-4-methoxy-2-oxo-3-butenoate with δ,ε-unsaturated alcohols has been found to be catalyzed by optically active complexes based on bis(oxazoline) (box) chiral ligands and copper(II) cations. The catalyst derived from the (S,S)-tert-Bu-bis(oxazoline) and Cu(SbF6)2 in the presence of 5 Å molecular sieves was highly effective to afford corresponding trans-fused hydropyranopyran derivatives in good yield (up to 90%) with high enantiomeric excess (up to 98% ee).

Keywords

intramolecular hetero Diels–Alder reaction; chiral Lewis acid catalyst; enantioselective reaction; tandem reaction; 1-oxa-1,3-butadiene; transetherification; molecular sieves