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Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates.
Org Lett. 2008 Aug 21; 10(16):3603-6.OL

Abstract

Dirhodium(II) tetrakis[ N-tetrachlorophthaloyl-(S)- tert-leucinate], Rh 2(S-TCPTTL) 4, is an exceptionally effective catalyst for enantioselective tandem carbonyl ylide formation-cycloaddition reactions of 2-diazo-3,6-diketoesters with arylacetylene, alkoxyacetylene, and styrene dipolarophiles, providing cycloadducts in good to high yields and with enantioselectivities of up to 99% ee as well as with perfect exo diastereoselectivity for styrenes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shimada N
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Anada M
No affiliation info available
Nakamura S
No affiliation info available
Nambu H
No affiliation info available
Tsutsui H
No affiliation info available
Hashimoto S
No affiliation info available

MeSH

AlkynesAzo CompoundsCarboxylic AcidsCatalysisCyclizationEpoxy CompoundsEstersKetonesMolecular StructureOrganometallic CompoundsRhodiumStereoisomerismStyrenes

Pub Type(s)

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

Language

eng

PubMed ID

18616257

Citation

Shimada, Naoyuki, et al. "Catalytic Enantioselective Intermolecular Cycloaddition of 2-diazo-3,6-diketoester-derived Carbonyl Ylides With Alkynes and Styrenes Using Chiral dirhodium(II) Carboxylates." Organic Letters, vol. 10, no. 16, 2008, pp. 3603-6.
Shimada N, Anada M, Nakamura S, et al. Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates. Org Lett. 2008;10(16):3603-6.
Shimada, N., Anada, M., Nakamura, S., Nambu, H., Tsutsui, H., & Hashimoto, S. (2008). Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates. Organic Letters, 10(16), 3603-6. https://doi.org/10.1021/ol8013733
Shimada N, et al. Catalytic Enantioselective Intermolecular Cycloaddition of 2-diazo-3,6-diketoester-derived Carbonyl Ylides With Alkynes and Styrenes Using Chiral dirhodium(II) Carboxylates. Org Lett. 2008 Aug 21;10(16):3603-6. PubMed PMID: 18616257.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates. AU - Shimada,Naoyuki, AU - Anada,Masahiro, AU - Nakamura,Seiichi, AU - Nambu,Hisanori, AU - Tsutsui,Hideyuki, AU - Hashimoto,Shunichi, Y1 - 2008/07/11/ PY - 2008/7/12/pubmed PY - 2008/10/22/medline PY - 2008/7/12/entrez SP - 3603 EP - 6 JF - Organic letters JO - Org Lett VL - 10 IS - 16 N2 - Dirhodium(II) tetrakis[ N-tetrachlorophthaloyl-(S)- tert-leucinate], Rh 2(S-TCPTTL) 4, is an exceptionally effective catalyst for enantioselective tandem carbonyl ylide formation-cycloaddition reactions of 2-diazo-3,6-diketoesters with arylacetylene, alkoxyacetylene, and styrene dipolarophiles, providing cycloadducts in good to high yields and with enantioselectivities of up to 99% ee as well as with perfect exo diastereoselectivity for styrenes. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/18616257/Catalytic_enantioselective_intermolecular_cycloaddition_of_2_diazo_36_diketoester_derived_carbonyl_ylides_with_alkynes_and_styrenes_using_chiral_dirhodium_II__carboxylates_ L2 - https://doi.org/10.1021/ol8013733 DB - PRIME DP - Unbound Medicine ER -