DIASTEREOSELECTIVE SYNTHESIS OF 2,3,4-TRISUBSTITUTED γ-LACTOLS AND γ-LACTONES VIA REGIO- AND STEREOCONTROLLED OPENING OF A 1,2-EPOXY-4-HYDROXYALKYL CARBAMATE WITH HETERO-NUCLEOPHILES

DOI: 10.1016/S0040-4039(00)84858-3

Source and publish data:

Tetrahedron Letters p. 3595 - 3598 (1986)

Update date:2022-08-04

Topics:

Authors:

Luessmann, Joerg

Hoppe, Dieter

Jones, Peter G.

Fittschen, Christa

Sheldrick, George M.

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Article abstract of DOI:10.1016/S0040-4039(00)84858-3

The acid-catalyzed ring opening of the title epoxide 1 takes place at the C-1 atom with retention of configuration at C-2 to form 2,3-cis-2-hydroxy-substituted γ-lactol derivatives 3.In basic media, nucleophiles attack the C-2 atom with inversion of confi

Full text of DOI:10.1016/S0040-4039(00)84858-3

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