Novel Diastereoselective Synthesis of Bicyclic β-Lactams through Radical Cyclization and Their Reduction toward 2-(1-Alkoxy-2-hydroxyethyl)piperidines and 2-(1-Alkoxy-2-hydroxyethyl)azepanes

Erika Leemans; Matthias D’hooghe; Yves Dejaegher; Karl W. Törnroos; Norbert De Kimpe

doi:10.1021/jo800550r

Novel Diastereoselective Synthesis of Bicyclic β-Lactams through Radical Cyclization and Their Reduction toward 2-(1-Alkoxy-2-hydroxyethyl)piperidines and 2-(1-Alkoxy-2-hydroxyethyl)azepanes

The Journal of Organic Chemistry ◽

10.1021/jo800550r ◽

2008 ◽

Vol 73 (9) ◽

pp. 3666-3666 ◽

Cited By ~ 1

Author(s):

Erika Leemans ◽

Matthias D’hooghe ◽

Yves Dejaegher ◽

Karl W. Törnroos ◽

Norbert De Kimpe

Keyword(s):

Radical Cyclization ◽

Diastereoselective Synthesis

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ChemInform Abstract: A Highly Diastereoselective Synthesis of cis-4a-Aryloctahydrocyclopenta(c)pyridine Derivatives Through Tandem Radical Cyclization of α-Amino Radical-Polyene Species.

ChemInform ◽

10.1002/chin.198914229 ◽

1989 ◽

Vol 20 (14) ◽

Author(s):

S. KANO ◽

Y. YUASA ◽

T. YOKOMATSU ◽

K. ASAMI ◽

S. SHIBUYA

Keyword(s):

Radical Cyclization ◽

Pyridine Derivatives ◽

Diastereoselective Synthesis ◽

Amino Radical

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Diastereoselective Synthesis of 4-Substituted L-Prolines by Intramolecular Radical Cyclization ofN-Aryl sulphonyl-N-allyl 3-bromoalanines: Interesting Dependence of Selectivity on the Nature of Sulphonamido Groups

Chemistry Letters ◽

10.1246/cl.2002.710 ◽

2002 ◽

Vol 31 (7) ◽

pp. 710-711 ◽

Cited By ~ 7

Author(s):

Amit Basak ◽

Subhendu Sekhar Bag ◽

Kakali Rani Rudra ◽

Jharna Barman ◽

Sumana Dutta

Keyword(s):

Radical Cyclization ◽

Diastereoselective Synthesis

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ChemInform Abstract: Diastereoselective Synthesis of Spiroketals via Radical Cyclization.

ChemInform ◽

10.1002/chin.199318100 ◽

2010 ◽

Vol 24 (18) ◽

pp. no-no

Author(s):

V. DALLA ◽

P. PALE

Keyword(s):

Radical Cyclization ◽

Diastereoselective Synthesis

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Radical Cyclization of Bromomethyldimethylsilyl Propargyl Ethers. Diastereoselective Synthesis of Functionalized Cyclopentanone Precursorsviaa (1,5) Hydrogen-Atom Transfer.

Synlett ◽

10.1055/s-1994-23063 ◽

1994 ◽

Vol 1994 (11) ◽

pp. 958-960 ◽

Cited By ~ 15

Author(s):

Stéphane Bogen ◽

Michel Journet ◽

Max Malacria

Keyword(s):

Hydrogen Atom ◽

Hydrogen Atom Transfer ◽

Radical Cyclization ◽

Atom Transfer ◽

Diastereoselective Synthesis

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Diastereoselective Synthesis of 2,6-Disubstituted 3-Hydroxy Piperidine Derivatives by an Application of Radical Cyclization

Heterocycles ◽

10.3987/com-91-5879 ◽

1991 ◽

Vol 32 (12) ◽

pp. 2311 ◽

Cited By ~ 11

Author(s):

Shiroshi Shibuya ◽

Yoko Yuasa ◽

Shinzo Kano

Keyword(s):

Radical Cyclization ◽

Diastereoselective Synthesis

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ChemInform Abstract: Diastereoselective Synthesis of Cyclic Ethers by Radical Cyclization at β-Position of β-Alkoxyacrylates.

ChemInform ◽

10.1002/chin.199726056 ◽

2010 ◽

Vol 28 (26) ◽

pp. no-no

Author(s):

Y. YUASA ◽

W. SATO ◽

S. SHIBUYA

Keyword(s):

Radical Cyclization ◽

Cyclic Ethers ◽

Diastereoselective Synthesis

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Diastereoselective Synthesis of Cyclopentapyridazinones via Radical Cyclization: Synthetic Studies Toward Halichlorine

Organic Letters ◽

10.1021/ol801849u ◽

2008 ◽

Vol 10 (21) ◽

pp. 4783-4786 ◽

Cited By ~ 13

Author(s):

Gary E. Keck ◽

Stacey A. Heumann

Keyword(s):

Radical Cyclization ◽

Diastereoselective Synthesis ◽

Synthetic Studies

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ChemInform Abstract: Diastereoselective Synthesis of 2,5-Disubstituted-3-hydroxy- pyrrolidine and 2,6-Disubstituted-3-hydroxypiperidine Derivatives by Radical Cyclization; Synthesis of (+)-Bulgecinine and (-)- Desoxoprosopinine.

ChemInform ◽

10.1002/chin.199634016 ◽

2010 ◽

Vol 27 (34) ◽

pp. no-no

Author(s):

Y. YUASA ◽

J. ANDO ◽

S. SHIBUYA

Keyword(s):

Radical Cyclization ◽

Diastereoselective Synthesis

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Aerobic copper-catalyzed oxidative [6C+1C] annulation: an efficient route to seven-membered carbocycles

Chemical Communications ◽

10.1039/c4cc03095h ◽

2014 ◽

Vol 50 (63) ◽

pp. 8764-8767 ◽

Cited By ~ 14

Author(s):

Xiao Liu ◽

Lingjuan Zhang ◽

Xianxiu Xu ◽

Shan Wang ◽

Ling Pan ◽

...

Keyword(s):

Michael Addition ◽

Oxidation Reaction ◽

Ethyl Cyanoacetate ◽

Radical Cyclization ◽

Diastereoselective Synthesis ◽

Ketene Dithioacetals ◽

Efficient Route

A copper-catalyzed aerobic tandem Michael addition–intramolecular radical cyclization–benzyl C(sp3)–H bond oxidation reaction of dicinnamoyl ketene dithioacetals and ethyl cyanoacetate was developed for the diastereoselective synthesis of seven-membered carbocycles.

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Substrate-Controlled Diastereoselective Synthesis of Sugar-Based Chlorinated Perhydrofuro[2,3-b]pyransviaCopper(I)-Catalyzed Radical Cyclization

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201600895 ◽

2017 ◽

Vol 359 (3) ◽

pp. 432-442 ◽

Cited By ~ 3

Author(s):

Ram N. Ram ◽

Neeraj Kumar ◽

Dharmendra Kumar Gupta

Keyword(s):

Radical Cyclization ◽

Diastereoselective Synthesis

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