Mg-promoted regio- and stereoselective C-acylation of aromatic α,/β-unsaturated carbonyl compounds

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3439-3442

  Ohno, Toshinobu ^b   Sakai, Masahiro ^a   Ishino, Yoshio ^b   Shibata, Toshihide ^a   Maekawa, Hirofumi ^a   Nishiguchi, Ikuzo ^a  

^a NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

^b OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000061272     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016376e     Document Type: Article

References (24)

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11. For recent reports on the generation and reaction of an acyl anion, see: (a) Scyfcrth, D.; Weinstein, R. M.; Hui, R. C.; Wang, W.-L.; Archer, C. M. J. Org. Chem. 1991, 56, 5768-5773.
12. (b) Ryu, I.: Hayama, Y.; Hirai, A.; Sonoda, N.; Orita, A.; One, K.; Murai, S. J. Am. Chem. Soc. 1990, 112, 7061-7063.
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18. Magnesium turnings for a Grignard reaction can be used without any pretreatment.
19. Although the detailed role of TMSCl is still unclear as described in our recent paper on Mg-promoted reductive cross-coupling of ethyl β-arylacylates with aldehydes, three main roles may be postulated, i.e., activation of the surface of magnesium metal, stabilization of anionic intermediates generated by electron transfer from magnesium, and activation of electrophiles by coordination to the oxygen atom of carbonyl compounds.
20. Ohno, T.; Ishino, Y.; Tsumagari, Y.; Nishiguchi, I. J. Org. Chem. 1995, 60, 458-460.
21. 13C NMR, MS, IR) and elemental analysis, as shown in Supporting Information.
22. Since acyl chlorides may also be able to activate the surface of magnesium metal, the reaction using acyl chlorides as acylating agents took place smoothly in the absence of TMSCl.
23. 3H-4H for 6a[A] and 6a[B] are 4.88 and 3.91 Hz.
24. Alberola, A.; Calvo, B.; Ortega, A. G.; Vicente, M.; Granda, S. G.; Maelen, J. F. J. Chem. Soc., Perkin Trans, 1 1991, 203-209.