Stereoselective synthesis of some chiral α-ferrocenyl carbenium ions

Chirality

Volumn 9, Issue 5-6, 1997, Pages 478-486

  Brunner, Andreas ^a   Taudien, Stefan ^a   Riant, Olivier ^a   Kagan, Henri B ^a  

^a CNRS   (France)

Author keywords

ferrocenyl carbenium ions; Catalyzed Diels Alder reaction; Diastereoselectivity; Lewis acid catalyst; Planar chirality

Indexed keywords

FERROCENE DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOMER; IONIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0030983954     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<478::AID-CHIR14>3.0.CO;2-L     Document Type: Article

References (8)

1. For some early works of enhanced stability of a carbenium center by a ferrocene moiety see references 2-4.
2. a: Richards, J.H., Hill, EA α-Metallocenyl carbonium ions. J. Am. Chem. Soc. 81:3484-3485, 1959.
3. b: Jutz, C. Methinfarbstoffe metallorganischer verbindungen diferrocenylmethin perchlorat. Tetrahedron Lett. 1:1-4, 1959.
4. Nesmeyanov, A.N., Sazonova, V.A., Drozol, V.N. Dokl. Akad. Nauk. SSSR 156:1393-1394, 1964,
5. Dokl. Chem. 192:154-159, 1964.
6. Gokel, G.W., Marquarding, D., Ugi, I.K. The retentive nucleophilic displacement of α-substituted alkylferrocenes. J. Org. Chem. 37:3052-3058, 1972.
7. Cais, M., Dani, S., Hernstein, F.H., Kapon, M. Determination of the crystal structure of α,α-diferrocenylmethylium tetrafluoroborate, a stable carbenium ion salt, and a comparison of its structure with those of other organometallic carbenium cations. J. Am. Chem. Soc. 100:5554-5558, 1978, and references quoted therein.
8. Allenmark, S. The synthetic use of α-ferrocenylcarbenium tetrafluoroborates. Tetrahedron Lett. 15:371-374, 1974.