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Synthesis of novel bidentate P-chiral diaminophosphine oxide preligands: application to Pd-catalyzed asymmetric allylic substitution reactions.
Chem Pharm Bull (Tokyo). 2011; 59(3):412-5.CP

Abstract

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.

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Authors+Show Affiliations

Harada T
Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan.
Nemoto T
No affiliation info available
Jin L
No affiliation info available
Hamada Y
No affiliation info available

MeSH

AlkylationAminationCatalysisOxidesPalladiumPhosphinesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21372429

Citation

Harada, Teisuke, et al. "Synthesis of Novel Bidentate P-chiral Diaminophosphine Oxide Preligands: Application to Pd-catalyzed Asymmetric Allylic Substitution Reactions." Chemical & Pharmaceutical Bulletin, vol. 59, no. 3, 2011, pp. 412-5.
Harada T, Nemoto T, Jin L, et al. Synthesis of novel bidentate P-chiral diaminophosphine oxide preligands: application to Pd-catalyzed asymmetric allylic substitution reactions. Chem Pharm Bull (Tokyo). 2011;59(3):412-5.
Harada, T., Nemoto, T., Jin, L., & Hamada, Y. (2011). Synthesis of novel bidentate P-chiral diaminophosphine oxide preligands: application to Pd-catalyzed asymmetric allylic substitution reactions. Chemical & Pharmaceutical Bulletin, 59(3), 412-5.
Harada T, et al. Synthesis of Novel Bidentate P-chiral Diaminophosphine Oxide Preligands: Application to Pd-catalyzed Asymmetric Allylic Substitution Reactions. Chem Pharm Bull (Tokyo). 2011;59(3):412-5. PubMed PMID: 21372429.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of novel bidentate P-chiral diaminophosphine oxide preligands: application to Pd-catalyzed asymmetric allylic substitution reactions. AU - Harada,Teisuke, AU - Nemoto,Tetsuhiro, AU - Jin,Long, AU - Hamada,Yasumasa, PY - 2011/3/5/entrez PY - 2011/3/5/pubmed PY - 2011/6/17/medline SP - 412 EP - 5 JF - Chemical & pharmaceutical bulletin JO - Chem Pharm Bull (Tokyo) VL - 59 IS - 3 N2 - 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. SN - 1347-5223 UR - https://www.unboundmedicine.com/medline/citation/21372429/Synthesis_of_novel_bidentate_P_chiral_diaminophosphine_oxide_preligands:_application_to_Pd_catalyzed_asymmetric_allylic_substitution_reactions_ L2 - https://joi.jlc.jst.go.jp/JST.JSTAGE/cpb/59.412?from=PubMed DB - PRIME DP - Unbound Medicine ER -