Synthesis of Novel Bidentate P-Chiral Diaminophosphine Oxide Preligands: Application to Pd-Catalyzed Asymmetric Allylic Substitution Reactions

Teisuke Harada; Tetsuhiro Nemoto; Long Jin; Yasumasa Hamada

doi:10.1248/cpb.59.412

Notes

Synthesis of Novel Bidentate P-Chiral Diaminophosphine Oxide Preligands: Application to Pd-Catalyzed Asymmetric Allylic Substitution Reactions

Teisuke Harada, Tetsuhiro Nemoto, Long Jin, Yasumasa Hamada

著者情報

キーワード: chiral diaminophosphine oxide, asymmetric allylic substitution, palladium, asymmetric catalysis, preligand

ジャーナルフリー

2011 年 59 巻 3 号 p. 412-415

DOI https://doi.org/10.1248/cpb.59.412

詳細

抄録

We developed a novel (S)-L-phenylalanine derived-bidentate chiral diaminophosphine oxide (DIAPHOX) preligand (S,S_P)-9b, which was successfully applied to Pd-catalyzed asymmetric allylic alkylation and amination. Using the Pd-(S,S_P)-9b catalyst system, asymmetric allylic alkylation and amination proceeded very smoothly, affording the corresponding products in excellent yield with high enantiomeric excess. It is noteworthy that both enantiomers were accessible with high enantiomeric purity using the structurally related DIAPHOX preligands (S,S_P)-9b and a monodentate chiral diaminophosphine oxide preligand (S,R_P)-10a, both of which can be prepared from a single chiral source, (S)-L-phenylalanine.

責任著者(Corresponding author)

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