ON THE PALLADIUM(II)-CATALYZED REARRANGEMENT OF ALLYL IMIDATES

被引：67

作者：

METZ, P

MUES, C

SCHOOP, A

机构：

[1] Organisch-Chemisches Institut der Universität Münster, D-4400 Münster

来源：

TETRAHEDRON | 1992年 / 48卷 / 06期

关键词：

PALLADIUM(II)-CATALYSIS; ALLYL IMIDATE REARRANGEMENT; CHIRALITY TRANSFER; (R)-N-(TRICHLOROACETYL)NORLEUCINOL;

D O I：

10.1016/S0040-4020(01)88203-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polyhetero-[3,3]-sigmatropic rearrangements of allyl N-phenylimidates 4a - f catalyzed by dichlorobis-(benzonitrile)palladium(II) are shown to afford N-allyl-N-phenylamides in good to excellent yields for substitution patterns that have so far precluded cyclization-induced allyl shifts. Using trichloroacetimidates of secondary allyl alcohols as substrates, the palladium(II)-catalyst effects a completely (E) stereoselective rearrangement at room temperature which proceeds with complete chirality transfer. This reaction has been applied to a synthesis of (R)-N-(trichloroacetyl)norleucinol (18) starting from (R)-2,3-O-isopropylidene glyceraldehyde (17).

引用

页码：1071 / 1080

页数：10

共 29 条

[1] SYNTHESIS OF(R)-EPICHLOROHYDRIN AND (S)-EPICHLOROHYDRIN [J].