Highly enantioselective Cu-catalysed asymmetric 1,4-addition of diphenylzinc to cyclohexenone

Chemical Communications

Volumn , Issue 16, 2004, Pages 1836-1837

  Peña, Diego ^a   López, Fernando ^a   Harutyunyan, Syuzanna R ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; COPPER; DIPHENYLZINC; LIGAND; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 4644252638     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b402868f     Document Type: Article

References (22)

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14. It is presumed that methylphenylzinc is formed in equilibrium with diphenylzinc and dimethylzinc. Apparently, the phenyl group is selectively transferred from that mixed zinc species. For the previous use of this concept in the asymmetric addition of diphenylzinc to aldehydes, see: (a) C. Bolm, N, Hermanns, J. P. Hildebrand and K. Muñiz, Angew. Chem., Int. Ed., 2001, 40, 3284; (b) J. Rudolph, T. Rasmussen, C. Bolm and P.-O. Norrby, Angew. Chem., Int. Ed., 2003, 42, 3002.
15. It is presumed that methylphenylzinc is formed in equilibrium with diphenylzinc and dimethylzinc. Apparently, the phenyl group is selectively transferred from that mixed zinc species. For the previous use of this concept in the asymmetric addition of diphenylzinc to aldehydes, see: (a) C. Bolm, N, Hermanns, J. P. Hildebrand and K. Muñiz, Angew. Chem., Int. Ed., 2001, 40, 3284; (b) J. Rudolph, T. Rasmussen, C. Bolm and P.-O. Norrby, Angew. Chem., Int. Ed., 2003, 42, 3002.
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17. It is known that biphenyl can be easily obtained from diphenylzinc. See for example: S. Hilpert and O. Grüttner, Chem. Ber., 1913, 46, 1675.
18. For instance, this occurs if samples were taken during the course of the reaction or if the solvent (toluene) was not freshly distilled from sodium under nitrogen and subsequently deoxygenated.
19. See Electronic Supplementary Information for details.
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