Diastereoselective ring-closing metathesis: synthesis of P-stereogenic phosphinates from prochiral phosphinic acid derivatives.

Journal article

[reaction: see text] The preparation of phosphorus-containing trienes featuring two diastereotopic vinyl moieties followed by a diastereoselective ring-closing metathesis is described. This methodology allowed for the synthesis of novel highly functionalized P-stereogenic heterocycles featuring both an exo- and an endocyclic double bond. An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis is also presented, revealing that the geometry of the double bonds conjugated to phosphorus is important and that 1,3-stereoinduction is superior to 1,4-stereoinduction for these reactions.

Authors: Dunne, K; Bisaro, F; Odell, B; Paris, J; Gouverneur, V

• Publication status: Published
• Journal: Journal of organic chemistry
• Volume: 70
• Issue: 26
• Pages: 10803-10809
• Publication date: 2005-12-01
• DOI: 10.1021/jo0518708
• EISSN: 1520-6904
• ISSN: 0022-3263
• Language: English