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

页码：7227 / 7232

页数：6

共 43 条

[41] Asymmetric Construction of Fluoroalkyl Tertiary Alcohols through a Three-Component Reaction of (Bpin)2, 1,3-Enynes, and Fluoroalkyl Ketones Catalyzed by a Copper(I) Complex (vol 20, pg 1070, 2018)
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ORGANIC LETTERS, 2018, 20 (06) : 1692 - 1692
[42] 1,4-Addition of arylboronic acids to β-aryl-α,β-unsaturated ketones and esters catalyzed by a rhodium(I)-chiraphos complex for catalytic and enantioselective synthesis of selective endothelin -: A receptor antagonists
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TETRAHEDRON, 2006, 62 (41) : 9610 - 9621
[43] A (2-(naphthalen-2-yl)phenyl)rhodium(i) complex formed by a proposed intramolecular 1,4-ortho-to-ortho′ Rh metal-atom migration and its efficacy as an initiator in the controlled stereospecific polymerisation of phenylacetylene
Tan, Nicholas Sheng Loong
Nealon, Gareth L.
Lynam, Jason M.
Sobolev, Alexandre N.
Rowles, Matthew R.
Ogden, Mark, I
Massi, Massimiliano
Lowe, Andrew B.
DALTON TRANSACTIONS, 2019, 48 (43) : 16437 - 16447

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