Journal ArticleDOI
Carbanion-Accelerated Claisen Rearrangements. 7. Phosphine Oxide and Phosphonate Anion Stabilizing Groups
Scott E. Denmark,John E. Marlin +1 more
TLDR
In this paper, the utility of phosphine oxide and phosphonate groups has been examined in the context of the carbanion-accelerated Claisen rearrangement (CACR), which permits the construction of substituted allyl vinyl ethers by allyl oxide addition to phosphorus-substituted allenes.Abstract:
The utility of phosphine oxide and phosphonate groups has been examined in the context of the carbanion-accelerated Claisen rearrangement (CACR). Both of the groups permit the construction of substituted allyl vinyl ethers by allyl oxide addition to phosphorus-substituted allenes. Extensive optimization was required to suppress isomerization of both the allenes and the vinyl ethers. Using potassium dimsylate and lithium chloride as the base, both the phosphine oxides and phosphonates rearranged readily at room temperature with complete regioselectivity in good yield (62-93%). The phosphonates also showed a high level of diastereoselectivity (92% de). The characteristic features of the CACR were compared with the original arylsulfone versionread more
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Journal ArticleDOI
Heterophosphacyclanes in organic synthesis
TL;DR: In this paper, a systematic account of the use of mono-and di-heterophosphacyclanes, containing σ3-, σ 4- and σ 5- phosphorus atoms, for the synthesis of phosphorus-free organic substances is given.
Journal ArticleDOI
An effective strategy for the preparation of (α,β-unsaturated hydrazones and pyrazole derivatives. Synthetic applications of β-functionalized phosphorus compounds.
TL;DR: In this article, β-Functionalized compounds are used for the synthesis of α,β-unsaturated hydrazones 1, pyrazoline 14 and pyrazole derivative 15.
Journal ArticleDOI
The synthesis of carbohydrate derivatives from acyclic precursors
David J. Ager,Michael B. East +1 more
Journal ArticleDOI
Double phosphinylation of propargylic alcohols: a novel synthetic route to 1,2-bis(diphenylphosphino)ethane derivatives.
TL;DR: Double phosphinylation of propargylic alcohols with diphenylphosphine oxide in the presence of a thiolate-bridged diruthenium complex as catalyst gives the corresponding 2,3-bis(diphenylPhosphinyl)-1-propenes in high yields with a complete selectivity.
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