通过亲核芳香取代合成手性氨基膦及其在钯催化对映选择性烯丙基取代中的应用。

Synthesis of chiral aminophosphines via nucleophilic aromatic substitution and their application to palladium-catalyzed enantioselective allylic substitution.

作者信息

Hattori T, Komuro Y, Hayashizaka N, Takahashi H, Miyano S

机构信息

Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University, Sendai, Japan.

出版信息

Enantiomer. 1997;2(3-4):203-13.

Abstract

Novel chiral aminophosphines, N,N-disubstituted diphenyl(1-amino-2-naphthyl)phosphines 4 were synthesized via nucleophilic aromatic substitution reaction on 1-methoxy-2-(diphenylphosphinoyl)naphthalene (1) by chiral lithium amides 2, followed by reduction of the phosphinoyl function. The new ligands were tested for their efficiency in the palladium-catalyzed allylic substitution of dimethyl malonate with 1,3-diphenyl-2-propenyl acetate and high asymmetric inductions up to 80%ee were observed.

摘要

新型手性氨基膦，即N,N-二取代二苯基(1-氨基-2-萘基)膦4，是通过手性锂酰胺2对1-甲氧基-2-(二苯基膦酰基)萘(1)进行亲核芳香取代反应，随后还原膦酰基官能团而合成的。测试了这些新配体在钯催化的丙二酸二甲酯与1,3-二苯基-2-丙烯基乙酸酯的烯丙基取代反应中的效率，观察到高达80%ee的高不对称诱导率。

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