Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration

被引：30
|
作者：
Partridge, Benjamin M. [1 ,3 ]
Callingham, Michael [1 ,2 ]
Lewis, William [1 ]
Lam, Hon Wai [1 ,2 ]
机构：
[1] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England
[2] Univ Nottingham, GSK Carbon Neutral Labs Sustainable Chem, Jubilee Campus, Nottingham NG7 2TU, England
[3] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 25期
基金：
英国工程与自然科学研究理事会;
关键词：
allylic compounds; cyclization; isomerization; reaction mechanisms; rhodium; C-H FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC ALLYLATION; RHODIUM; ALCOHOLS; PALLADIUM; LIGANDS; IMINES;
D O I：
10.1002/anie.201703155
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Alkenyl-to-allyl 1,4-rhodium(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C-H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3-enyne tethered to a ketone, to give products containing three contiguous stereocenters. The products can be obtained in high enantioselectivities using a chiral sulfur-alkene ligand.
引用
收藏
页码：7227 / 7232
页数：6
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