Volume 31, Issue 25
Preparative Organic Chemistry
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ChemInform Abstract: Chiral Diphenylthiophosphoramides: A New Class of Chiral Ligands for the Silver(I)-Promoted Enantioselective Allylation of Aldehydes.

Min Shi

Min Shi

Lab. Organomet. Chem., Shanghai Inst. Org. Chem., Acad. Sin., Shanghai 200032, Peop. Rep. China

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Wen-Sheng Sui

Wen-Sheng Sui

Lab. Organomet. Chem., Shanghai Inst. Org. Chem., Acad. Sin., Shanghai 200032, Peop. Rep. China

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First published: 07 June 2010

Abstract

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ChemInform Abstract

For the first time it is demonstrated that chiral phosphoryl sulfides catalyze the enantioselective allylation of aldehydes with tributylallyltin using Ag(I) salt. By means of the novel chiral thiophosphoramide TPA, under optimized conditions secondary (R)-alcohols are obtained with moderate enantioselectivities. Utilizing bis(thiophosphoramides) (VI) as chiral ligands, the enantioselectivities of alcohol (IIIa) reach only 9-15%.

chemical structure image

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