Regiodivergent Ligand-Controlled Rhodium-Catalyzed [(2+2)+2] Carbocyclization Reactions with Alkyl Substituted Methyl Propiolates

被引：44

作者：

Evans, P. Andrew ^{[1
]}

Sawyer, James R. ^{[2
]}

Inglesby, Phillip A. ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[2] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 33期

基金：

美国国家卫生研究院; 英国工程与自然科学研究理事会;

关键词：

carbocyclization; diastereoselective; metallacycle; regiodivergent reactions; rhodium; 1,6-ENYNES; CYCLOADDITION; COMPLEXES; COBALT; CONSTRUCTION; DIENES; ENYNES;

D O I：

10.1002/anie.201002117

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Choice is yours: In the title reaction the selective formation of either regioisomer can be controlled through judicious choice of the ancillary ligands (see scheme). Central to this accomplishment was the realization that residual silver salts from the salt metathesis of the neutral complex have a strong effect on the regio- and diastereoselectivity. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5746 / 5749

页数：4

共 50 条

[31] A Concise Total Synthesis of Pyrovellerolactone Using a Rhodium-Catalyzed [(3+2)+2] Carbocyclization Reaction
Evans, P. Andrew
Inglesby, Phillip A.
Kilbride, Kathryn
ORGANIC LETTERS, 2013, 15 (08) : 1798 - 1801
[32] Rhodium-Catalyzed Regiodivergent [3+2] and [5+2] Cycloadditions of Quinolinium Ylides with Alkynes
He, Min
Chen, Nuan
Wang, Jian
Peng, Shiyong
ORGANIC LETTERS, 2019, 21 (13) : 5167 - 5171
[33] Rhodium-Catalyzed Oxygenative [2+2] Cycloaddition of Terminal Alkynes and Imines for the Synthesis of β-Lactams
Kim, Insu
Roh, Sang Weon
Lee, Dong Gil
Lee, Chulbom
ORGANIC LETTERS, 2014, 16 (09) : 2482 - 2485
[34] Diastereoselective intermolecular rhodium-catalyzed [4+2+2] carbocyclization reactions: Computational and experimental evidence for the intermediacy of an alternative metallacycle intermediate
Baik, MH
Baum, EW
Burland, MC
Evans, PA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (06) : 1602 - 1603
[35] Ligand-controlled cobalt-catalyzed regiodivergent hydroboration of aryl,alkyl-disubstituted internal allenes
Wu, Caizhi
Ge, Shaozhong
CHEMICAL SCIENCE, 2020, 11 (10) : 2783 - 2789
[36] Ligand-controlled regiodivergent Ni-catalyzed trans-hydroboration/carboboration of internal alkynes with B2pin2
Chen, Zunsheng
Nie, Biao
Li, Xiaoning
Liu, Teng
Li, Chunsheng
Huang, Jiuzhong
CHEMICAL SCIENCE, 2024, 15 (06) : 2236 - 2242
[37] Rhodium-Catalyzed [(3+2)+1] Carbocyclization Reactions of Alkynylidenecyclopropanes with Carbon Monoxide: Regiospecific Construction of Polysubstituted Phenols
Evans, P. Andrew
Burnie, Andrew J.
Negru, Daniela E.
ORGANIC LETTERS, 2014, 16 (17) : 4356 - 4359
[38] RHODIUM-CATALYZED [2+2+2] CYCLOADDITION FOR THE SYNTHESIS OF SUBSTITUTED PYRIDINES, PYRIDONES, AND THIOPYRANIMINES
Tanaka, Ken
HETEROCYCLES, 2012, 85 (05) : 1017 - 1043
[39] Rhodium-Catalyzed Intermolecular [2+2] Cycloaddition of Terminal Alkynes with Electron-Deficient Alkenes
Sakai, Kazunori
Kochi, Takuya
Kakiuchi, Fumitoshi
ORGANIC LETTERS, 2013, 15 (05) : 1024 - 1027
[40] Stereoselective rhodium(I)-catalyzed [(3+2)+1] and [(3+2)+2] carbocyclization reactions
Negru, Daniela E.
Shang, Deju
Evans, P. Andrew
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245

← 1 2 3 4 5 →