Catalytic asymmetric allylic C-H activation as a surrogate of the asymmetric Claisen rearrangement

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3587-3590

  Davies, Huw M L ^a   Ren, Pingda ^a   Jin, Qihui ^a  

^a UNIVERSITY AT BUFFALO   (United States)

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ARTICLE;

EID: 0000835722     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0167255     Document Type: Article

References (33)

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15. Aryldiazoacetates and vinyldiazoacetates have been used as carbenoid precursors in asymmetric intermolecular C-H insertions. Other diazo compounds that generate chemoselective donor/acceptor substituted carbenoids are alkynyldiazoacetates and heteroaryldiazoacetates. For a general review, see: Davies, H. M. L.: Antoulinakis, E. G. J. Organomet. Chem. 2001, 617-618, 47
16. (a) Davies, H. M. L.; Antoulinakis, E. G.; Hansen, T. Org. Lett. 1999, 1, 383.
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31. The absolute configuration of 4 was determined to be (R) by comparison to a known sample (see ref 12b). The absolute configuration of the other C-H insertion products is assigned by analogy.
32. Relative stereochemistry is readily achived on the basis of distinctive chemical shifts in the proton NMR. For details, see: Davies, H. M. L.; Ren, P. Tetrahedron Lett. 2001, 42, 3149.
33. The determination of the relative and absolute stereochemistry for 16 and 17 is described in detail in Supporting Information.