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Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by eta6-arene/TsDPEN-ruthenium(II) complexes.
Org Lett. 2007 Jan 18; 9(2):255-7.OL

Abstract

Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta6-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations. [reaction: see text].

Authors+Show Affiliations

Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan. ohkuma@eng.hokudai.ac.jpNo 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

17217278

Citation

Ohkuma, Takeshi, et al. "Asymmetric Hydrogenation of Alpha-chloro Aromatic Ketones Catalyzed By eta6-arene/TsDPEN-ruthenium(II) Complexes." Organic Letters, vol. 9, no. 2, 2007, pp. 255-7.
Ohkuma T, Tsutsumi K, Utsumi N, et al. Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by eta6-arene/TsDPEN-ruthenium(II) complexes. Org Lett. 2007;9(2):255-7.
Ohkuma, T., Tsutsumi, K., Utsumi, N., Arai, N., Noyori, R., & Murata, K. (2007). Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by eta6-arene/TsDPEN-ruthenium(II) complexes. Organic Letters, 9(2), 255-7.
Ohkuma T, et al. Asymmetric Hydrogenation of Alpha-chloro Aromatic Ketones Catalyzed By eta6-arene/TsDPEN-ruthenium(II) Complexes. Org Lett. 2007 Jan 18;9(2):255-7. PubMed PMID: 17217278.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by eta6-arene/TsDPEN-ruthenium(II) complexes. AU - Ohkuma,Takeshi, AU - Tsutsumi,Kunihiko, AU - Utsumi,Noriyuki, AU - Arai,Noriyoshi, AU - Noyori,Ryoji, AU - Murata,Kunihiko, PY - 2007/1/16/pubmed PY - 2007/3/21/medline PY - 2007/1/16/entrez SP - 255 EP - 7 JF - Organic letters JO - Org Lett VL - 9 IS - 2 N2 - Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta6-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations. [reaction: see text]. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17217278/Asymmetric_hydrogenation_of_alpha_chloro_aromatic_ketones_catalyzed_by_eta6_arene/TsDPEN_ruthenium_II__complexes_ L2 - https://doi.org/10.1021/ol062661s DB - PRIME DP - Unbound Medicine ER -