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Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adduct derivatives using chiral diaminophosphine oxides: DIAPHOXs.
Org Lett. 2007 Mar 01; 9(5):927-30.OL

Abstract

[reaction: see text] Asymmetric allylic amination of allylic carbonates prepared from racemic Morita-Baylis-Hillman adducts proceeded in the presence of Pd catalyst, chiral diaminophosphine oxide (DIAPHOX), and BSA, affording the corresponding chiral aza-Morita-Baylis-Hillman adduct derivatives in excellent yield with up to 99% ee. The cyclic reaction products could be converted into various synthetically useful compounds such as chiral cyclic beta-amino acids.

Authors+Show Affiliations

Nemoto T
Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 263-8522, Japan.
Fukuyama T
No affiliation info available
Yamamoto E
No affiliation info available
Tamura S
No affiliation info available
Fukuda T
No affiliation info available
Matsumoto T
No affiliation info available
Akimoto Y
No affiliation info available
Hamada Y
No affiliation info available

MeSH

CatalysisMolecular StructureOxidesPalladiumPhosphinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

17284046

Citation

Nemoto, Tetsuhiro, et al. "Pd-catalyzed Asymmetric Allylic Amination of Morita-Baylis-Hillman Adduct Derivatives Using Chiral Diaminophosphine Oxides: DIAPHOXs." Organic Letters, vol. 9, no. 5, 2007, pp. 927-30.
Nemoto T, Fukuyama T, Yamamoto E, et al. Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adduct derivatives using chiral diaminophosphine oxides: DIAPHOXs. Org Lett. 2007;9(5):927-30.
Nemoto, T., Fukuyama, T., Yamamoto, E., Tamura, S., Fukuda, T., Matsumoto, T., Akimoto, Y., & Hamada, Y. (2007). Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adduct derivatives using chiral diaminophosphine oxides: DIAPHOXs. Organic Letters, 9(5), 927-30.
Nemoto T, et al. Pd-catalyzed Asymmetric Allylic Amination of Morita-Baylis-Hillman Adduct Derivatives Using Chiral Diaminophosphine Oxides: DIAPHOXs. Org Lett. 2007 Mar 1;9(5):927-30. PubMed PMID: 17284046.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Pd-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman adduct derivatives using chiral diaminophosphine oxides: DIAPHOXs. AU - Nemoto,Tetsuhiro, AU - Fukuyama,Takashi, AU - Yamamoto,Eri, AU - Tamura,Shinji, AU - Fukuda,Tomoaki, AU - Matsumoto,Takayoshi, AU - Akimoto,Yuichi, AU - Hamada,Yasumasa, Y1 - 2007/02/07/ PY - 2007/2/8/pubmed PY - 2007/5/1/medline PY - 2007/2/8/entrez SP - 927 EP - 30 JF - Organic letters JO - Org Lett VL - 9 IS - 5 N2 - [reaction: see text] Asymmetric allylic amination of allylic carbonates prepared from racemic Morita-Baylis-Hillman adducts proceeded in the presence of Pd catalyst, chiral diaminophosphine oxide (DIAPHOX), and BSA, affording the corresponding chiral aza-Morita-Baylis-Hillman adduct derivatives in excellent yield with up to 99% ee. The cyclic reaction products could be converted into various synthetically useful compounds such as chiral cyclic beta-amino acids. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17284046/Pd_catalyzed_asymmetric_allylic_amination_of_Morita_Baylis_Hillman_adduct_derivatives_using_chiral_diaminophosphine_oxides:_DIAPHOXs_ L2 - https://doi.org/10.1021/ol0700207 DB - PRIME DP - Unbound Medicine ER -