Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

DOI: 10.1016/S0040-4039(00)60383-0

Source and publish data:

Tetrahedron Letters p. 2203 - 2206 (1993)

Update date:2022-08-02

Topics:

Authors:

Clayden, Jonathan

Collington, Eric W.

Brian Lamount

Warren, Stuart

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Article abstract of DOI:10.1016/S0040-4039(00)60383-0

Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereo specifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

Full text of DOI:10.1016/S0040-4039(00)60383-0

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