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Enantioselective cycloaddition of carbonyl ylides with arylallenes using Rh2(S-TCPTTL)4.
Org Biomol Chem. 2013 Aug 28; 11(32):5374-82.OB

Abstract

The first catalytic asymmetric carbonyl ylide cycloaddition with arylallenes is described. With dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, the cycloaddition of carbonyl ylides derived from diazoketoesters with arylallenes proceeded in a fully chemo- and regioselective manner to give highly functionalized 8-oxabicyclo[3.2.1]octanes with up to 99% ee and perfect exo diastereoselectivity.

Authors+Show Affiliations

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, 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

23852012

Citation

Krishnamurthi, Janagiraman, et al. "Enantioselective Cycloaddition of Carbonyl Ylides With Arylallenes Using Rh2(S-TCPTTL)4." Organic & Biomolecular Chemistry, vol. 11, no. 32, 2013, pp. 5374-82.
Krishnamurthi J, Nambu H, Takeda K, et al. Enantioselective cycloaddition of carbonyl ylides with arylallenes using Rh2(S-TCPTTL)4. Org Biomol Chem. 2013;11(32):5374-82.
Krishnamurthi, J., Nambu, H., Takeda, K., Anada, M., Yamano, A., & Hashimoto, S. (2013). Enantioselective cycloaddition of carbonyl ylides with arylallenes using Rh2(S-TCPTTL)4. Organic & Biomolecular Chemistry, 11(32), 5374-82. https://doi.org/10.1039/c3ob41236a
Krishnamurthi J, et al. Enantioselective Cycloaddition of Carbonyl Ylides With Arylallenes Using Rh2(S-TCPTTL)4. Org Biomol Chem. 2013 Aug 28;11(32):5374-82. PubMed PMID: 23852012.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective cycloaddition of carbonyl ylides with arylallenes using Rh2(S-TCPTTL)4. AU - Krishnamurthi,Janagiraman, AU - Nambu,Hisanori, AU - Takeda,Koji, AU - Anada,Masahiro, AU - Yamano,Akihito, AU - Hashimoto,Shunichi, PY - 2013/7/16/entrez PY - 2013/7/16/pubmed PY - 2014/2/6/medline SP - 5374 EP - 82 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 11 IS - 32 N2 - The first catalytic asymmetric carbonyl ylide cycloaddition with arylallenes is described. With dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, the cycloaddition of carbonyl ylides derived from diazoketoesters with arylallenes proceeded in a fully chemo- and regioselective manner to give highly functionalized 8-oxabicyclo[3.2.1]octanes with up to 99% ee and perfect exo diastereoselectivity. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/23852012/Enantioselective_cycloaddition_of_carbonyl_ylides_with_arylallenes_using_Rh2_S_TCPTTL_4_ L2 - https://doi.org/10.1039/c3ob41236a DB - PRIME DP - Unbound Medicine ER -