Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 2015-2021

  Thominiaux, Cyrille ^a   Roussé, Sébastien ^a   Desmaële, Didier ^a   D'Angelo, Jean ^a   Riche, Claude ^b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLCYCLOPENTANONE; ALKENE; ALPHA METHYLBENZYLAMINE; CYCLOPENTANONE DERIVATIVE; ESTER; IMINE; PROPYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033591118     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00180-9     Document Type: Article

References (12)

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2. Reviews: (a) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751-762. (b) Perlmutter, P. In Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992; Chap. 6, pp. 299-337.
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4. For leading references, see: (a) Blarer, S. J.; Seebach, D. Chem. Ber. 1983, 116, 2250-2260 and 3086-3096. (b) Felluga, F.; Nitti, P.; Pitacco, G.; Valentin E. J. Chem. Res. (S), 1992, 86-87.
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7. (a) Cavé, C.; Desmaële, D.; d'Angelo, J.; C. Riche, C. J. Org. Chem. 1996, 61, 4361-4368.
8. (b) Tran Huu Dau, M. E.; Riche, C.; Dumas, C.; d'Angelo, J. Tetrahedron: Asymmetry 1998, 9, 1059-1064.
9. McMurry, J. E.; Melton, J. J. Am. Chem. Soc. 1971, 93, 5309-5311.
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12. It should be pointed out, that in sharp contrast with the five-membered ring series, addition of imine 19 to 2-nitropropene 7 unexpectedly furnished a mixture of diketones 20 and 21 in the 6:1 ratio, in 35% yield. (matrix presented)