Catalytic enantioselective intermolecular cycloadditions of a 2-diazo-3,6-diketoester-derived carbonyl ylide with alkyne and strained alkene dipolarophiles

Tetrahedron Asymmetry

Volumn 14, Issue 7, 2003, Pages 921-924

  Hodgson, David M ^a   Labande, Agnès H ^a   Glen, Rebecca ^a   Redgrave, Alison J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; CARBONYL DERIVATIVE; HEPTANOIC ACID DERIVATIVE; NORBORNENE DERIVATIVE; PHENYLACETIC ACID; PHOSPHATE; TERT BUTYL 2 DIAZO 3,6 DIOXOHEPTANOIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; CYCLOADDITION; DECOMPOSITION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 0037418808     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00036-3     Document Type: Article

References (31)

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19. Enantioselective carbonyl ylide type cycloadditions of (aromatic) oxidopyryliums have also been reported: Kitagaki, S.; Yasugahira, M.; Anada, M.; Nakajima, M.; Hashimoto, S. Tetrahedron Lett. 2000, 41, 5931-5935 (up to 93% ee using DMAD); Suga, H.; Inoue, K.; Inoue, S.; Kakehi, A. J. Am. Chem. Soc. 2002, 124, 14836-14837 (up to 98% ee using an 3-acryloyl-2-oxazolidinone with a chiral Lewis acid-Rh catalyst combination).
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22. 3N, MeCN, 84%).
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24. 8.
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28. The X-ray crystal structure analysis of compound 9 will be reported elsewhere.
29. -1).
30. +): calc. 324.2175, measured 324.2173.
31. 3).