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Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine.
Org Lett. 2007 Oct 25; 9(22):4559-62.OL

Abstract

Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or alpha,beta-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenylsulfonyl)-alpha-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (-)-metazocine.

Authors+Show Affiliations

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

17894504

Citation

Anada, Masahiro, et al. "Catalytic Enantioselective Amination of Silyl Enol Ethers Using Chiral dirhodium(II) Carboxylates: Asymmetric Formal Synthesis of (-)-metazocine." Organic Letters, vol. 9, no. 22, 2007, pp. 4559-62.
Anada M, Tanaka M, Washio T, et al. Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine. Org Lett. 2007;9(22):4559-62.
Anada, M., Tanaka, M., Washio, T., Yamawaki, M., Abe, T., & Hashimoto, S. (2007). Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine. Organic Letters, 9(22), 4559-62.
Anada M, et al. Catalytic Enantioselective Amination of Silyl Enol Ethers Using Chiral dirhodium(II) Carboxylates: Asymmetric Formal Synthesis of (-)-metazocine. Org Lett. 2007 Oct 25;9(22):4559-62. PubMed PMID: 17894504.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine. AU - Anada,Masahiro, AU - Tanaka,Masahiko, AU - Washio,Takuya, AU - Yamawaki,Minoru, AU - Abe,Takumi, AU - Hashimoto,Shunichi, Y1 - 2007/09/26/ PY - 2007/9/27/pubmed PY - 2008/1/8/medline PY - 2007/9/27/entrez SP - 4559 EP - 62 JF - Organic letters JO - Org Lett VL - 9 IS - 22 N2 - Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or alpha,beta-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenylsulfonyl)-alpha-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (-)-metazocine. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17894504/Catalytic_enantioselective_amination_of_silyl_enol_ethers_using_chiral_dirhodium_II__carboxylates:_asymmetric_formal_synthesis_of_____metazocine_ L2 - https://doi.org/10.1021/ol702019b DB - PRIME DP - Unbound Medicine ER -