Diastereoselective synthesis of ferrocenyl sulfoximines with planar and central chirality

被引:67
作者
Bolm, C [1 ]
Kesselgruber, M [1 ]
Muñiz, K [1 ]
Raabe, G [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1021/om991041a
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The capability of the sulfonimidoyl moiety to serve as ortho-directing group for the diastereoselective lithiation of enantiopure ferrocenylsulfoximines is demonstrated. (S)-N-p-Tolylsulfonyl-S-ferrocenyl-S-tert-butylsulfoximine showed excellent diastereoselectivity concerning planar chirality of the products obtained after quenching of the lithium species with several electrophiles. Various electrophiles (MeI, Me2S2, Me3SiCl, p-anisaldehyde, acetone, 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 configuration of the products was determined by chemical correlation and X-ray crystallographic analysis of(S,R-p)-N-p-tolylsulfonyl-S-tert-butyl-S-(2-iodoferrocenyl)sulfoximine. Taking into account the structure of the starting material, the ortho-directing effect can be ascribed to the oxygen atom of the sulfoximine.
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收藏
页码:1648 / 1651
页数:4
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