Grignard 1,4-Additions to para-Substituted (2R)-N-Cinnamoylbornane-10,2-sultam Derivatives: Revised Configuration for the N,OAc-Keteneacetal Formation in the Presence of Cu(I)

被引：1

作者：

Piatek, Anna ^{[1
]}

Chapuis, Christian ^{[2
,3
]}

机构：

[1] Univ Warsaw, Dept Chem, Pasteura 1, PL-02093 Warsaw, Poland

[2] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

[3] Firmenich Co, Corp R&D Div, POB 239, CH-1211 Geneva 8, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2016年 / 99卷 / 08期

关键词：

Grignard; 1; 4-addition; Conjugated; Michael additions; Cinnamoyl; Sultam; N-ENOYL-SULTAMS; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; DIASTEREOSELECTIVE CONJUGATE ADDITION; DIELS-ALDER REACTIONS; ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; BETA-DISUBSTITUTED; (E)-ENOYLSULTAMS; CATALYZED 1,4-ADDITION; HYDROXYAMINO ACIDS;

D O I：

10.1002/hlca.201500521

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Using a F-19-NMR analytical method, we have corrected and improved the linear correlation initially found between the diastereoselectivity observed during the EtMgBr conjugated addition to Michael acceptors of type 1, as a function of their sigma(para)Hammett electronic parameters. Based on H-1-NMR analyses, we have also discovered that the original configuration of the acetylated intermediate, obtained by either hydride, Grignard, or cuprate conjugate additions to -substituted N-enoyl bornane-10,2-sultams was initially erroneously attributed by Oppolzer et al. A new, much simpler rationalization for these 1,4-additions has now been proposed.

引用

页码：573 / 582

页数：10