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  4. Homochiral Matching in the Diels-Alder Clyclodimerization 2-Vinyl-7-Oxabicyclo[2.2.1]Hept-2-Ene Derivatives
 
research article

Homochiral Matching in the Diels-Alder Clyclodimerization 2-Vinyl-7-Oxabicyclo[2.2.1]Hept-2-Ene Derivatives

Meerpoel, L.
•
Vrahami, M. M.
•
Ancerewicz, J.
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1994
Tetrahedron Letters

Racemic 6-vinyl-7-oxabicyclo[2.2.1]hept-5-en-2-one, 5-vinyl-7-oxabicyclo[2.2.1]hept-5-en-2-one and their ethylene acetals undergo highly stereoselective Diels-Alder cyclodimerizations. The optically pure semicyclic dienes give the corresponding optically pure dimers with the same ease.

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Type
research article
DOI
10.1016/0040-4039(94)88176-6
Author(s)
Meerpoel, L.
Vrahami, M. M.
Ancerewicz, J.
Vogel, P.  
Date Issued

1994

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

35

Issue

1

Start page

111

End page

114

Subjects

Face selectivity

•

[4+2]-cycloadditions

•

chiral recognition

•

(1r

•

2s

•

3s

•

4r

•

7r

•

11s

•

12r)-11-ethenyl-15

•

16-dioxapentacyclo[10.2.1.1(4

•

7).

•

0(3

•

8).0(2.11)]hexadec-8-en-6

•

13-dione

•

(1r

•

2r

•

3r

•

4r

•

7r

•

11r

•

12r)-11-ethen

•

yl-15

•

16-dioxapentacyclo[10.2.1.1(4

•

7).0(3

•

8).0(2.11)]hexadec-8-en-5

•

14-

•

dione and their ethylene acetals

•

Naked sugars

•

regioselectivity

•

stereochemistry

•

dimerization

Note

Univ lausanne,chim sect,ch-1005 lausanne,switzerland.

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219693
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