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N,N'-dioxide-Cu(OTf)(2) complex catalyzed highly enantioselective amination reaction of N-acetyl enamide.
Org Lett. 2010 May 21; 12(10):2214-7.OL

Abstract

The N,N'-dioxide-Cu(OTf)(2) complexes were applied in the asymmetric amination reaction of N-acetyl enamides with dialkyl azodicarboxylate, giving the corresponding products in good yields with high enantioselectivities (up to 91% ee). Precursors of vicinal diamine were readily obtained with excellent diastereoselectivities (>95:5) by NaBH(4) reduction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chang L
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
Kuang Y
No affiliation info available
Qin B
No affiliation info available
Zhou X
No affiliation info available
Liu X
No affiliation info available
Lin L
No affiliation info available
Feng X
No affiliation info available

MeSH

AmidesAminationCatalysisCopperDiaminesMesylatesMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20402479

Citation

Chang, Lu, et al. "N,N'-dioxide-Cu(OTf)(2) Complex Catalyzed Highly Enantioselective Amination Reaction of N-acetyl Enamide." Organic Letters, vol. 12, no. 10, 2010, pp. 2214-7.
Chang L, Kuang Y, Qin B, et al. N,N'-dioxide-Cu(OTf)(2) complex catalyzed highly enantioselective amination reaction of N-acetyl enamide. Org Lett. 2010;12(10):2214-7.
Chang, L., Kuang, Y., Qin, B., Zhou, X., Liu, X., Lin, L., & Feng, X. (2010). N,N'-dioxide-Cu(OTf)(2) complex catalyzed highly enantioselective amination reaction of N-acetyl enamide. Organic Letters, 12(10), 2214-7. https://doi.org/10.1021/ol100540p
Chang L, et al. N,N'-dioxide-Cu(OTf)(2) Complex Catalyzed Highly Enantioselective Amination Reaction of N-acetyl Enamide. Org Lett. 2010 May 21;12(10):2214-7. PubMed PMID: 20402479.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - N,N'-dioxide-Cu(OTf)(2) complex catalyzed highly enantioselective amination reaction of N-acetyl enamide. AU - Chang,Lu, AU - Kuang,Yulong, AU - Qin,Bo, AU - Zhou,Xin, AU - Liu,Xiaohua, AU - Lin,Lili, AU - Feng,Xiaoming, PY - 2010/4/21/entrez PY - 2010/4/21/pubmed PY - 2010/8/13/medline SP - 2214 EP - 7 JF - Organic letters JO - Org Lett VL - 12 IS - 10 N2 - The N,N'-dioxide-Cu(OTf)(2) complexes were applied in the asymmetric amination reaction of N-acetyl enamides with dialkyl azodicarboxylate, giving the corresponding products in good yields with high enantioselectivities (up to 91% ee). Precursors of vicinal diamine were readily obtained with excellent diastereoselectivities (>95:5) by NaBH(4) reduction. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20402479/NN'_dioxide_Cu_OTf__2__complex_catalyzed_highly_enantioselective_amination_reaction_of_N_acetyl_enamide_ L2 - https://doi.org/10.1021/ol100540p DB - PRIME DP - Unbound Medicine ER -