A Scalable Synthesis of Chiral Himbert Diene Ligands for Asymmetric Catalysis

被引：0

作者：

Rit, Raja K. ^{[1
,2
]}

Li, Hongyi ^{[1
,2
]}

Argent, Stephen P. ^{[2
]}

Wheelhouse, Katherine M. ^{[3
]}

Woodward, Simon ^{[1
,2
]}

Lam, Hon Wai ^{[1
,2
]}

机构：

[1] Univ Nottingham, GlaxoSmithKline Carbon Neutral Labs Sustainable Ch, Jubilee Campus, Triumph Rd, Nottingham NG7 2TU, England

[2] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England

[3] GlaxoSmithKline, GSK Med Res Ctr, Gunnels Wood Rd, Stevenage SG1 2NY, Hertfordshire, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric catalysis; chiral dienes; enantioselectivity; rhodium; DIELS-ALDER REACTION; ARYLBORONIC ACIDS; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; 1,4-ADDITION REACTIONS; N-TOSYL; ALPHA; BETA-UNSATURATED CARBONYL; ORGANOBORONIC ACIDS; CYCLIC IMINES; BORONIC ACIDS;

D O I：

10.1002/adsc.202300039

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chiral dienes are important ligands in asymmetric catalysis but they are less accessible than other commonly used ligands such as chiral bisphosphines. Here, we show that intramolecular [4+2] cycloaddition of a simply attained chiral allenecarboxanilide readily affords pseudoenantiomeric bicyclo[2.2.2]octa-2,5-dienes containing an alkenyl bromide, which can be readily functionalized to give diverse chiral diene ligands. The synthesis is straightforward and easily conducted on multigram scales. These ligands exhibit high performance in nine types of enantioselective Rh(I)-catalyzed 1,4-addition or 1,2-addition reactions.

引用

页码：1629 / 1639

页数：11

共 112 条

[1] Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands [J].