Successively Recycle Waste as Catalyst: A One-Pot Wittig/1,4-Reduction/Paal-Knorr Sequence for Modular Synthesis of Substituted Furans

被引：66

作者：

Chen, Long ^{[1
]}

Du, Yi ^{[2
]}

Zeng, Xing-Ping ^{[1
]}

Shi, Tao-Da ^{[1
]}

Zhou, Feng ^{[1
]}

Zhou, Jian ^{[1
,3
]}

机构：

[1] E China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Med, Xinhua Hosp, Shanghai 200092, Peoples R China

[3] Shanghai Inst Organ Chem, CAS, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 06期

关键词：

PHOSPHINE-INITIATED REACTIONS; PAAL-KNORR REACTION; BETA-AMINO ESTERS; O BOND FORMATION; POLYSUBSTITUTED FURANS; TETRASUBSTITUTED FURANS; ENANTIOSELECTIVE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; (2-FURYL)CARBENE COMPLEXES;

D O I：

10.1021/acs.orglett.5b00442

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot tandem Wittig/conjugate reduction/PaalKnorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.

引用

页码：1557 / 1560

页数：4

共 86 条

[1] Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol [J].

Alaimo, Peter J. ;

O'Brien, Robert ;

Johnson, Adam W. ;

Slauson, Sarah R. ;

O'Brien, Jeannette M. ;

Tyson, Elizabeth L. ;

Marshall, Amanda-Lynn ;

Ottinger, Colleen E. ;

Chacon, Jon G. ;

Wallace, Lorien ;

Paulino, Corey Y. ;

Connell, Sarah .

ORGANIC LETTERS, 2008, 10 (22) :5111-5114

[2] Generation of α,β-Unsaturated Platinum Carbenes from Homopropargylic Alcohols: Rearrangements to Polysubstituted Furans [J].

Allegretti, Paul A. ;

Ferreira, Eric M. .

ORGANIC LETTERS, 2011, 13 (21) :5924-5927

[3] Green Chemistry: Principles and Practice [J].

Anastas, Paul ;

Eghbali, Nicolas .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312

[4] Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes [J].

Barluenga, Jose ;

Riesgo, Lorena ;

Vicente, Ruben ;

Lopez, Luis A. ;

Tomas, Miguel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13528-+

[5] Bioinspired organocatalytic asymmetric reactions [J].

Bernardi, Luca ;

Fochi, Mariafrancesca ;

Franchini, Mauro Comes ;

Ricci, Alfredo .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (15) :2911-2922

[6] Developments in furan syntheses [J].

Brown, RCD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) :850-852

[7] Copper-Catalyzed C-O Bond Formation: An Efficient One-Pot Highly Regioselective Synthesis of Furans from (2-Furyl)Carbene Complexes [J].

Cao, Hua ;

Zhan, Haiying ;

Cen, Jinghe ;

Lin, Jingxin ;

Lin, Yuanguang ;

Zhu, Qiuxia ;

Fu, Minling ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2013, 15 (05) :1080-1083

[8] Improving the Atom Efficiency of the Wittig Reaction by a "Waste as Catalyst/Co-catalyst" Strategy [J].

Cao, Jun-Jie ;

Zhou, Feng ;

Zhou, Jian .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) :4976-4980

[9] Tandem and domino catalytic strategies for enantioselective synthesis [J].

Chapman, Christopher J. ;

Frost, Christopher G. .

SYNTHESIS-STUTTGART, 2007, (01) :1-21

[10] Diversified assembly of perfluoroalkyl-substituted furans and 2,5-dihydrofuran-2-ols [J].

Chen, Guofei ;

He, Guangke ;

Xue, Can ;

Fu, Chunling ;

Ma, Shengming .

TETRAHEDRON LETTERS, 2011, 52 (02) :196-198

← 1 2 3 4 5 6 7 8 9 →