Homochiral Matching in the Diels-Alder Cyclodimerization of 2-Vinyl-7-oxabicyclohept-2-ene Derivatives.

DOI: 10.1016/0040-4039(94)88176-6

Source and publish data:

Tetrahedron Letters p. 111 - 114 (1994)

Update date:2022-08-02

Topics:

Authors:

Meerpoel, Lieven

Vrahami, Maria-Miranda

Ancerewicz, Jacek

Vogel, Pierre

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Article abstract of DOI:10.1016/0040-4039(94)88176-6

Keywords: 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-ethenyl-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.Abstract: 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.

Full text of DOI:10.1016/0040-4039(94)88176-6

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Product name:2-endo-acetoxy-6-exo-(phenylselenenyl)-5-endo-bromo-7-oxabicyclo<2.2.1>heptane-2-exo-carbonitrile

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