STEREOCONTROL IN RADICAL CYCLIZATION: STEREOSELECTIVE SYNTHESIS OF 2,4-CIS AND 2,4-TRANS TETRAHYDROFURAN DERIVATIVES VIA MONO- OR DICHLOROMETHYL RADICAL.

DOI: 10.1016/S0040-4039(00)80085-4

Source and publish data:

Tetrahedron Letters p. 321 - 324 (1988)

Update date:2022-07-29

Topics:

Authors:

Watanabe, Yoshihiko

Endo, Takeshi

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Article abstract of DOI:10.1016/S0040-4039(00)80085-4

A novel stereocontrol method for the preparation of 2,4-disubstituted tetrahydrofurans was presented. 2,4-Cis-disubstituted-3,3-dichlorotetrahydrofurans 2 were provided predominantly by the radical cyclization of allyl-2,2,2-trichloroethylethers 1 with tributyltin hydride.The effect of geometry of chlorine atom and olefin on products stereochemistry was also discussed.

Full text of DOI:10.1016/S0040-4039(00)80085-4

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