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Literature DB >> 17429998

Reactions of nitroso hetero-Diels-Alder cycloadducts with azides: stereoselective formation of triazolines and aziridines.

Abstract

The addition of azides to acylnitroso hetero-Diels-Alder cycloadducts derived from cyclopentadiene affords exo-triazolines in excellent yield. The reaction is greatly affected by the level of alkene strain, while sterically demanding azides do not hinder the reaction. Conversion of the triazolines to aziridines is also described.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17429998 PMCID： PMC3170844 DOI： 10.1021/jo0701987

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

25 in total

1. Synthesis of enantiomerically and diastereomerically pure 2(S)-amino-6(R)-hydroxy-1,7-heptanedioic acid dimethyl ester hydrochloride from cycloheptadiene.

Authors: B T Shireman; M J Miller
Journal: J Org Chem Date: 2001-07-13 Impact factor: 4.354

2. Catalytic asymmetric claisen rearrangement in natural product synthesis: synthetic studies toward (-)-xeniolide F.

Authors: Annett Pollex; Martin Hiersemann
Journal: Org Lett Date: 2005-12-08 Impact factor: 6.005

3. The synthesis and in vitro testing of structurally novel antibiotics derived from acylnitroso Diels-Alder adducts.

Authors: George P Nora; Marvin J Miller; Ute Möllmann
Journal: Bioorg Med Chem Lett Date: 2006-05-26 Impact factor: 2.823

4. Chemoenzymatic asymmetric total synthesis of phosphodiesterase inhibitors: preparation of a polycyclic pyrazolo[3,4-d]pyrimidine from an acylnitroso Diels-Alder cycloadduct-derived aminocyclopentenol.

Authors: May Xiao-Wu Jiang; Namal C Warshakoon; Marvin J Miller
Journal: J Org Chem Date: 2005-04-01 Impact factor: 4.354

5. Regio- and stereochemically controlled formation of hydroxamic acid containing anti- or syn-1,4-cycloalkenols from acylnitroso-derived Diels-Alder adducts.

Authors: M D Surman; M J Miller
Journal: J Org Chem Date: 2001-04-06 Impact factor: 4.354

6. Organic azides: an exploding diversity of a unique class of compounds.

Authors: Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal: Angew Chem Int Ed Engl Date: 2005-08-19 Impact factor: 15.336

7. Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer.

Authors: Fangzheng Li; John B Brogan; Jennifer L Gage; Deyi Zhang; Marvin J Miller
Journal: J Org Chem Date: 2004-06-25 Impact factor: 4.354

8. concise synthesis of 4-acylamino analogues of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acids (LY354740) from an acylnitroso Diels-Alder cycloadduct.

Authors: Wenlin Lee; Marvin J Miller
Journal: J Org Chem Date: 2004-06-25 Impact factor: 4.354

9. First synthesis of 2',3'-epimino-carbocyclic nucleosides.

Authors: Minoru Ishikura; Atsushi Murakami; Nobuya Katagiri
Journal: Org Biomol Chem Date: 2003-02-07 Impact factor: 3.876

10. Hetero Diels-Alder reactions of nitrosoamidines: an efficient method for the synthesis of functionalized guanidines.

Authors: Craig A Miller; Robert A Batey
Journal: Org Lett Date: 2004-03-04 Impact factor: 6.005

8 in total

1. Continuous flow of nitroso Diels-Alder reaction.

Authors: Erika Nakashima; Hisashi Yamamoto
Journal: Chem Commun (Camb) Date: 2015-08-07 Impact factor: 6.222

2. Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Authors: Cheng Ji; Marvin J Miller
Journal: Tetrahedron Lett Date: 2010-07-01 Impact factor: 2.415

Reactions of nitroso hetero-Diels-Alder cycloadducts with azides: stereoselective formation of triazolines and aziridines.

1. Synthesis of enantiomerically and diastereomerically pure 2(S)-amino-6(R)-hydroxy-1,7-heptanedioic acid dimethyl ester hydrochloride from cycloheptadiene.

2. Catalytic asymmetric claisen rearrangement in natural product synthesis: synthetic studies toward (-)-xeniolide F.

3. The synthesis and in vitro testing of structurally novel antibiotics derived from acylnitroso Diels-Alder adducts.

4. Chemoenzymatic asymmetric total synthesis of phosphodiesterase inhibitors: preparation of a polycyclic pyrazolo[3,4-d]pyrimidine from an acylnitroso Diels-Alder cycloadduct-derived aminocyclopentenol.

5. Regio- and stereochemically controlled formation of hydroxamic acid containing anti- or syn-1,4-cycloalkenols from acylnitroso-derived Diels-Alder adducts.

6. Organic azides: an exploding diversity of a unique class of compounds.

7. Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer.

8. concise synthesis of 4-acylamino analogues of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acids (LY354740) from an acylnitroso Diels-Alder cycloadduct.

9. First synthesis of 2',3'-epimino-carbocyclic nucleosides.

10. Hetero Diels-Alder reactions of nitrosoamidines: an efficient method for the synthesis of functionalized guanidines.

1. Continuous flow of nitroso Diels-Alder reaction.

2. Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.

Review 3. The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

4. Brønsted acid-mediated opening of nitroso cycloadducts under anhydrous conditions.

5. Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.

6. Diastereoselective synthesis of a spironoraristeromycin using an acylnitroso Diels-Alder reaction.

7. Synthesis and photophysical investigation of squaraine rotaxanes by "clicked capping".

8. Acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols.