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Literature DB >> 20161491

Iminonitroso ene reactions: experimental studies on reactivity, regioselectivity and enantioselectivity.

Abstract

Ene reactions of iminonitroso agents with olefins were investigated in both solution and solid phase. Reactions afforded allyl hydroxylamine products in up to 99% yield and with high regioselectivity. A Cu(I)-mediated enantioselective nitroso ene reaction gave an ene product with up to 40% ee.

Entities: Chemical

Year: 2010 PMID： 20161491 PMCID： PMC2796777 DOI： 10.1016/j.tetlet.2009.11.015

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

18 in total

1. Allylic Amination.

Authors: Mogens Johannsen; Karl Anker Jørgensen
Journal: Chem Rev Date: 1998-06-18 Impact factor: 60.622

Review 2. The nitroso ene reaction: a regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential.

Authors: Waldemar Adam; Oliver Krebs
Journal: Chem Rev Date: 2003-10 Impact factor: 60.622

3. Efficient pi-facial control in the ene reaction of nitrosoarene, triazolinedione, and singlet oxygen with tiglic amides of the bornane-derived sultam as chiral auxiliary: an economical synthesis of enantiomerically pure nitrogen- and oxygen-functionalized acrylic acid derivatives.

Authors: Waldemar Adam; Hans-Georg Degen; Oliver Krebs; Chantu R Saha-Möller
Journal: J Am Chem Soc Date: 2002-11-06 Impact factor: 15.419

4. Variable Markovnikov orientation and "cis effect" in ene reactions of nitrosocarbonyl intermediates.

Authors: Paolo Quadrelli; Mariella Mella; Andrea Piccanello; Silvano Romano; Pierluigi Caramella
Journal: J Org Chem Date: 2007-02-02 Impact factor: 4.354

5. An experimental and computational study on the reactivity and regioselectivity for the nitrosoarene ene reaction: comparison with triazolinedione and singlet oxygen.

Authors: W Adam; N Bottke; B Engels; O Krebs
Journal: J Am Chem Soc Date: 2001-06-13 Impact factor: 15.419

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

Authors: Weimin Lin; Anuradha Gupta; Kyung Hee Kim; David Mendel; Marvin J Miller
Journal: Org Lett Date: 2009-01-15 Impact factor: 6.005

7. Diels-Alder and ene reactions of singlet oxygen, nitroso compounds and triazolinediones: transition states and mechanisms from contemporary theory.

Authors: Andrew G Leach; K N Houk
Journal: Chem Commun (Camb) Date: 2002-06-21 Impact factor: 6.222

8. Control of regioselectivity by the lone substituent through steric and electronic effects in the nitrosoarene ene reaction of deuterium-labeled trisubstituted alkenes.

Authors: Waldemar Adam; Oliver Krebs; Michael Orfanopoulos; Manolis Stratakis
Journal: J Org Chem Date: 2002-11-29 Impact factor: 4.354

9. Catalytic, highly enantio, and diastereoselective nitroso diels-alder reaction.

Authors: Yuhei Yamamoto; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2004-04-07 Impact factor: 15.419

10. Syntheses and biological activity studies of novel sterol analogs from nitroso Diels-Alder reactions of ergosterol.

Authors: Baiyuan Yang; Patricia A Miller; Ute Möllmann; Marvin J Miller
Journal: Org Lett Date: 2009-07-02 Impact factor: 6.005

1 in total

1. N-O chemistry for antibiotics: discovery of N-alkyl-N-(pyridin-2-yl)hydroxylamine scaffolds as selective antibacterial agents using nitroso Diels-Alder and ene chemistry.

Authors: Timothy A Wencewicz; Baiyuan Yang; James R Rudloff; Allen G Oliver; Marvin J Miller
Journal: J Med Chem Date: 2011-09-15 Impact factor: 7.446

1 in total