The remarkable crossed co-isomerization reaction of cyclopropyl ketones and enones via nickeladihydropyrans

Angewandte Chemie - International Edition

Volumn 45, Issue 41, 2006, Pages 6788-6790

  Lloyd Jones, Guy C ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Cyclopropanes; Enolates; Enones; Homogeneous catalysis; Nickel

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; ISOMERIZATION; NICKEL COMPOUNDS;

CYCLOPROPANES; ENOLATES; ENONES; HOMOGENEOUS CATALYSIS;

KETONES;

EID: 33750484992     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602629     Document Type: Short Survey

References (17)

1. For selected recent examples, see: a) C. Böing, G. Franciò, W. Leitner, Adv. Synth. Catal. 2005, 347, 1537-1541;
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5. S. Ogoshi, M. Nagata, H Kurosawa, J. Am. Chem. Soc. 2006, 128, 5350-5351.
6. L. Liu, J. Montgomery, J. Am. Chem. Soc. 2006, 128, 5348-5349.
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11. Curiously, the schemes in reference [3] are suggestive of processes that are stoichiometric in nickel; however, experimental procedures given in the supporting information clearly indicate that 5 or 10 mol% Ni complex is employed.
12. a) H. P. Hratchian, S. K. Chowdury, V. M. Gutiérrez-García, K. K. D. Amarasinghe, M. J. Heeg, H. B. Schlegel, J. Montgomery, Organometallics 2004, 23, 4636-4646, and references therein;
13. for a discussion of O-bound versus C-bound Ni (and Pd) enolates, see: b) J. Cámpora, C. M. Maya, P. Palma, E. Carmona, E. Gutiérrez, C. Ruiz, C. Graiff, A. Tiripicchio, Chem. Eur. J. 2005, 11, 6889-6904.
14. Reaction in THF allows 5 (R = Ph) to be isolated in 25 % yield as an analytically pure, fully characterized, orange solid.
15. 2-keto complex 11. Whilst not directly translatable to the conditions developed by Montgomery (reference [3]), this result explains why slow addition of enone is crucial for success under catalytic conditions.
16. 3]. No mention of thermally triggered reductive elimination, for example, in the presence of 1, is made.
17. 3P or NHC).