DIELS-ALDER REACTIONS OF 1,3-DIENYLBORONATES AS A NEW ROUTE TO FUNCTIONALIZED CARBOCYCLES.

DOI: 10.1016/S0040-4039(00)95569-2

Source and publish data:

Tetrahedron Letters p. 4169 - 4172 (1987)

Update date:2022-08-16

Topics:

Authors:

Vaultier, Michel

Truchet, Francoise

Carboni, Bertrand

Hoffmann, Reinhard W.

Denne, Ingrid

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Article abstract of DOI:10.1016/S0040-4039(00)95569-2

Hydroboration of enynes with various hydroborating agents followed by refunctionalization at boron furnished 1,3-dienylboronates which undergo clean Diels-Alder addition to typical dienophiles.The resulting adducts contain an allylboronate functionality.Accordingly they add to aldehydes in a highly stereoselective fashion establishing the relative configuration at up to four stereogenic centers.

Full text of DOI:10.1016/S0040-4039(00)95569-2

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