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Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates.
Org Lett. 2011 Dec 02; 13(23):6284-7.OL

Abstract

The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh(2)(S-TCPTTL)(4), gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.

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 available

Pub Type(s)

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

Language

eng

PubMed ID

22047068

Citation

Shimada, Naoyuki, et al. "Catalytic Enantioselective Intermolecular Cycloaddition of Diazodiketoester-derived Carbonyl Ylides With Indoles Using Chiral dirhodium(II) Carboxylates." Organic Letters, vol. 13, no. 23, 2011, pp. 6284-7.
Shimada N, Oohara T, Krishnamurthi J, et al. Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates. Org Lett. 2011;13(23):6284-7.
Shimada, N., Oohara, T., Krishnamurthi, J., Nambu, H., & Hashimoto, S. (2011). Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates. Organic Letters, 13(23), 6284-7. https://doi.org/10.1021/ol2027625
Shimada N, et al. Catalytic Enantioselective Intermolecular Cycloaddition of Diazodiketoester-derived Carbonyl Ylides With Indoles Using Chiral dirhodium(II) Carboxylates. Org Lett. 2011 Dec 2;13(23):6284-7. PubMed PMID: 22047068.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective intermolecular cycloaddition of diazodiketoester-derived carbonyl ylides with indoles using chiral dirhodium(II) carboxylates. AU - Shimada,Naoyuki, AU - Oohara,Tadashi, AU - Krishnamurthi,Janagiraman, AU - Nambu,Hisanori, AU - Hashimoto,Shunichi, Y1 - 2011/11/02/ PY - 2011/11/4/entrez PY - 2011/11/4/pubmed PY - 2012/2/9/medline SP - 6284 EP - 7 JF - Organic letters JO - Org Lett VL - 13 IS - 23 N2 - The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh(2)(S-TCPTTL)(4), gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22047068/Catalytic_enantioselective_intermolecular_cycloaddition_of_diazodiketoester_derived_carbonyl_ylides_with_indoles_using_chiral_dirhodium_II__carboxylates_ DB - PRIME DP - Unbound Medicine ER -