Diastereoselective synthesis of ferrocenyl sulfoximines with planar and central chirality

Citation
C. Bolm et al., Diastereoselective synthesis of ferrocenyl sulfoximines with planar and central chirality, ORGANOMETAL, 19(9), 2000, pp. 1648-1651
Citations number
55
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
0276-7333 → ACNP
Volume
19
Issue
9
Year of publication
2000
Pages
1648 - 1651
Database
ISI
SICI code
0276-7333(20000501)19:9<1648:DSOFSW>2.0.ZU;2-R
Abstract
The capability of the sulfonimidoyl moiety to serve as ortho-directing grou p for the diastereoselective lithiation of enantiopure ferrocenylsulfoximin es is demonstrated. (S)-N-p-Tolylsulfonyl-S-ferrocenyl-S-tert-butylsulfoxim ine showed excellent diastereoselectivity concerning planar chirality of th e products obtained after quenching of the lithium species with several ele ctrophiles. Various electrophiles (MeI, Me2S2, Me3SiCl, p-anisaldehyde, ace tone, n-Bu3SnCl, I-2) were introduced in yields from 36 to 78%. Only up to 10% of product substituted at both the cyclopentadienyl ring and the phenyl group of the tosyl moiety was isolated as byproduct. The relative configur ation of the products was determined by chemical correlation and X-ray crys tallographic analysis of(S,R-p)-N-p-tolylsulfonyl-S-tert-butyl-S-(2-iodofer rocenyl)sulfoximine. Taking into account the structure of the starting mate rial, the ortho-directing effect can be ascribed to the oxygen atom of the sulfoximine.