- Solid phase synthesis of alkenes using the Horner-Wadsworth-Emmons reaction and monitoring by gel phase 31P NMR
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Phosphonoacetamide esters bound to solid supported peptides or peptide synthesis supports are active as Horner-Wadsworth-Emmons (HWE) reagents with a variety of aldehydes. HWE reagents can be attached to the solid support via the amide or phosphono ester. Mild basic conditions, triethylamine and Li salts, with excess aldehyde give high conversions to alkenes.
- Johnson,Zhang
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- Direct substitution of primary allylic amines with sulfinate salts
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The NH2 group in primary allylic amines was substituted directly by sulfinate salts with excellent regio- and stereoselectivities. In the presence of 0.1 mol % [Pd(allyl)Cl]2, 0.4 mol % 1,4- bis(diphenylphosphino)butane (dppb), and excess boric acid, a range of α-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an α-selective fashion to give structurally diverse allylic sulfones in good to excellent yields with exclusive E selectivity. Replacing dppb with 1,1′-bi-2-naphthol (BINOL) allowed unsymmetric α-chiral primary allylic amines to be transformed into the corresponding allylic sulfones in good to excellent yields with excellent retention of ee. Importantly, the reaction complements known asymmetric methods in substrate scope via its unique ability to provide α-chiral allylic sulfones with high optical purity starting from unsymmetric allylic electrophiles.
- Wu, Xue-Song,Chen, Yan,Li, Man-Bo,Zhou, Meng-Guang,Tian, Shi-Kai
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supporting information
p. 14694 - 14697
(2012/11/07)
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