Palladium/Lewis Acid Co-catalyzed Divergent Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Alcohols

被引：53

作者：

Yang, Fan ^{[1
]}

Chen, Jingchao ^{[1
]}

Xu, Jianbin ^{[1
]}

Ma, Fujie ^{[1
]}

Zhou, Yongyun ^{[1
]}

Shinde, Madhuri Vikas ^{[1
]}

Fan, Baomin ^{[1
]}

机构：

[1] Yunnan Minzu Univ, YMU HKBU Joint Lab Tradit Nat Med, Kunming 650500, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

基金：

中国国家自然科学基金;

关键词：

AZABICYCLIC ALKENES; OXABICYCLIC ALKENES; TRANSFER HYDROGENATION; ALPHA; BETA-UNSATURATED KETONES; AMINE NUCLEOPHILES; COMPLEXES; OXABENZONORBORNADIENES; (+)-HOMOCHELIDONINE; ALKALOIDS; PROGRESS;

D O I：

10.1021/acs.orglett.6b02300

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By fine tuning the combinations of chiral palladium catalysts and Lewis acids, both the additional and reductive asymmetric ring-opening reactions of azabenzonorbornadienes with alcohols were accomplished with good chemoselectivity, regioselectivity, and enantioselectivity. It was proven that the reductive ring-opening products were generated through a transfer hydrogenation process with alcohols as hydrogen source.

引用

页码：4832 / 4835

页数：4

共 42 条

[11] Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a PdII-catalyzed ring-opening strategy [J].

Fleming, Matthew J. ;

McManus, Helen A. ;

Rudolph, Alena ;

Chan, Walter H. ;

Ruiz, Jeremy ;

Dockendorff, Chris ;

Lautens, Mark .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (07) :2112-2124

[12] Highly diastereoselective synthesis of nucleoside adducts from the carcinogenic benzo[a]pyrene diol epoxide and a computational analysis [J].

Lakshman, Mahesh K. ;

Keeler, John C. ;

Ngassa, Felix N. ;

Hilmer, John H. ;

Pradhan, Padmanava ;

Zajc, Barbara ;

Thomasson, Kathryn A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (01) :68-76

[13] Enantioselective ring opening of aza and oxabicyclic alkenes with dimethylzinc [J].

Lautens, M ;

Hiebert, S ;

Renaud, JL .

ORGANIC LETTERS, 2000, 2 (13) :1971-1973

[14] Scope of the nickel catalyzed asymmetric reductive ring opening reaction. Synthesis of enantiomerically enriched cyclohexenols. [J].

Lautens, M ;

Rovis, T .

TETRAHEDRON, 1998, 54 (07) :1107-1116

[15] Rhodium-catalyzed asymmetric alcoholysis and aminolysis of oxabenzonorbornadiene: A new enantioselective carbon-heteroatom bond forming process [J].

Lautens, M ;

Fagnou, K ;

Rovis, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5650-5651

[16] Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: Application of halide effects in the development of a general process [J].

Lautens, M ;

Fagnou, K ;

Yang, DQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14884-14892

[17] Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with sulfur nucleophiles [J].

Leong, P ;

Lautens, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :2194-2196

[18] Asymmetric reductive ring-opening of bicyclic olefins catalyzed by palladium and nickel complexes [J].

Li, LP ;

Rayabarapu, DK ;

Nandi, M ;

Cheng, CH .

ORGANIC LETTERS, 2003, 5 (10) :1621-1624

[19] Palladium/Zinc Co-Catalyzed syn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols [J].

Li, Sifeng ;

Xu, Jianbin ;

Fan, Baomin ;

Lu, Zhiwu ;

Zeng, Chaoyuan ;

Bian, Zhaoxiang ;

Zhou, Yongyun ;

Wang, Jun .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (25) :9003-9007

[20] Asymmetric Alkynylative Ring Opening Reaction of Oxabenzonorbornadienes Promoted by Palladium/Silver Cocatalytic System [J].

Liu, Shanshan ;

Li, Sifeng ;

Chen, Hualei ;

Yang, Qingjing ;

Xu, Jianbin ;

Zhou, Yongyun ;

Yuan, Minglong ;

Zeng, Weimin ;

Fan, Baomin .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) :2960-2964

← 1 2 3 4 5 →