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Volumn 19, Issue 25, 2013, Pages 8342-8351

Catalytic asymmetric synthesis of spirocyclic azlactones by a double Michael-addition approach

Author keywords

5+1 cycloaddition; asymmetric catalysis; domino reactions; palladacycle; spiro compounds; twist conformation

Indexed keywords

ASYMMETRIC CATALYSIS; CONTIGUOUS STEREOCENTERS; DOMINO REACTIONS; ENANTIOSELECTIVE FORMATION; PALLADACYCLES; PLANAR CHIRAL FERROCENE; SPECTROSCOPIC STUDIES; SPIRO COMPOUNDS;

EID: 84878834803     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300224     Document Type: Article
Times cited : (59)

References (140)
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    • CCDC-918517 (trans- 3 j, major diastereomer and enantiomer), CCDC-918519 (trans- 3 a), CCDC-918526 (trans- 3 d), CCDC-918518 (trans- 3 l, major diastereomer), and CCDC-918524 (trans- 3 e) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC-918517 (trans- 3 j, major diastereomer and enantiomer), CCDC-918519 (trans- 3 a), CCDC-918526 (trans- 3 d), CCDC-918518 (trans- 3 l, major diastereomer), and CCDC-918524 (trans- 3 e) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
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    • CCDC 918527 (trans- 3 l, minor diastereomer) contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 918527 (trans- 3 l, minor diastereomer) contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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    • CCDC-918522 (cis- 3 a), CCDC-918523 (cis- 3 b), CCDC-918528 (cis- 3 h), CCDC-918525 (cis- 3 i) and CCDC-918521 (cis- 3 m) contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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    • C. Yu, Y. Zhang, A. Song, Y. Ji, W. Wang, Chem. Eur. J. 2011, 17, 770. To investigate if dynamic kinetic resolution might also play a role in our study, we have examined if the formation of 11 and 12 is reversible. The isolated compounds 11 and 12 were thus treated with the usual reaction conditions of the catalysis. Regioisomeric mixtures have indeed been obtained by using the single regioisomers. However, the equilibration is rather slow (see the Supporting Information). In contrast, the formation of the S,S-configured spirocyclic product trans -3 a was found to be irreversible (see the Supporting Information). Treating the isolated diastereomerically pure material under the usual reaction conditions does not form any R,S-configured isomer and trans -3 a was reisolated in quantitative yield with an unchanged ee value of 95 %. Based on the slow retro-Michael reaction of the initial 1,4-addition product in combination with the very rapid and irreversible intramolecular Michael addition, a dynamic kinetic resolution is unlikely to have a large impact in the present case.
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    • This often exclusive preference is also generally found for nonferrocene-derived palladacycles, see, for example, ref. [15 b] and references cited therein, and, D. S. Black, G. B. Deacon, G. L. Edwards, Aust. J. Chem. 1994, 47, 217.
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    • For the rearrangement of allylic imidates with planar chiral palladacycle catalysts, computational studies have shown that coordination of the neutral substrates trans to the N donor results in significantly lower activation barriers:, M. P. Watson, L. E. Overman, R. G. Bergman, J. Am. Chem. Soc. 2007, 129, 5031.
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    • see ref. [4 b]
    • see ref. [4 b]
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    • See ref. [31] and
    • See ref. [31] and
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    • CCDC-918520 (20) contains the supplementary crystallographic data. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.