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Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.
Angew Chem Int Ed Engl. 2013 Dec 16; 52(51):13601-5.AC

Abstract

Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies.

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Authors+Show Affiliations

Shu XZ
School of Pharmacy, University of Wisconsin, Madison, WI 53705-2222 (USA).
Schienebeck CM
No affiliation info available
Song W
No affiliation info available
Guzei IA
No affiliation info available
Tang W
No affiliation info available

MeSH

AlkynesCatalysisCyclizationCycloaddition ReactionMolecular StructureRhodiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24150975

Citation

Shu, Xing-Zhong, et al. "Transfer of Chirality in the Rhodium-catalyzed Intramolecular [5+2] Cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and Alkynes: Synthesis of Enantioenriched Bicyclo[5.3.0]decatrienes." Angewandte Chemie (International Ed. in English), vol. 52, no. 51, 2013, pp. 13601-5.
Shu XZ, Schienebeck CM, Song W, et al. Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes. Angew Chem Int Ed Engl. 2013;52(51):13601-5.
Shu, X. Z., Schienebeck, C. M., Song, W., Guzei, I. A., & Tang, W. (2013). Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes. Angewandte Chemie (International Ed. in English), 52(51), 13601-5. https://doi.org/10.1002/anie.201306919
Shu XZ, et al. Transfer of Chirality in the Rhodium-catalyzed Intramolecular [5+2] Cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and Alkynes: Synthesis of Enantioenriched Bicyclo[5.3.0]decatrienes. Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13601-5. PubMed PMID: 24150975.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes. AU - Shu,Xing-Zhong, AU - Schienebeck,Casi M, AU - Song,Wangze, AU - Guzei,Ilia A, AU - Tang,Weiping, Y1 - 2013/10/21/ PY - 2013/08/06/received PY - 2013/10/24/entrez PY - 2013/10/24/pubmed PY - 2014/11/5/medline KW - catalysis KW - enynes KW - polycyclic compounds KW - rhodium KW - stereospecific reactions SP - 13601 EP - 5 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 52 IS - 51 N2 - Chiral bicycles: Enantioenriched bicyclo[5.3.0]decatrienes were prepared from readily available chiral 3-acyloxy-1,4-enynes (ACEs) for the first time. In most cases, the chirality of the ACEs could be transferred to the bicyclic products with high efficiency. Inversion of the configuration was observed, thus confirming the predictions of previous computational studies. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/24150975/Transfer_of_chirality_in_the_rhodium_catalyzed_intramolecular_[5+2]_cycloaddition_of_3_acyloxy_14_enynes__ACEs__and_alkynes:_synthesis_of_enantioenriched_bicyclo[5_3_0]decatrienes_ L2 - https://doi.org/10.1002/anie.201306919 DB - PRIME DP - Unbound Medicine ER -