Literature DB >> 21438516

Allene functionalization via bicyclic methylene aziridines.

Luke A Boralsky1, Dagmara Marston, R David Grigg, John C Hershberger, Jennifer M Schomaker.   

Abstract

The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. This paper describes the use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons.
© 2011 American Chemical Society

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Year:  2011        PMID: 21438516      PMCID: PMC3090038          DOI: 10.1021/ol2002418

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  13 in total

1.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Rh(II)-catalysed room temperature aziridination of homoallyl-carbamates.

Authors:  Christopher J Hayes; Peter W Beavis; Lesley A Humphries
Journal:  Chem Commun (Camb)       Date:  2006-11-21       Impact factor: 6.222

3.  Spirodiepoxide reaction with cuprates.

Authors:  Partha Ghosh; Stephen D Lotesta; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2007-02-09       Impact factor: 15.419

4.  Spirodiepoxides: heterocycle synthesis and mechanistic insight.

Authors:  Stephen D Lotesta; Sezgin Kiren; Ronald R Sauers; Lawrence J Williams
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  N-tosyloxycarbamates as a source of metal nitrenes: rhodium-catalyzed C-H insertion and aziridination reactions.

Authors:  Hélène Lebel; Kim Huard; Sylvain Lectard
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

6.  The allylic azide rearrangement: achieving selectivity.

Authors:  Alina K Feldman; Benoît Colasson; K Barry Sharpless; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2005-10-05       Impact factor: 15.419

7.  Spirodiepoxides in total synthesis: epoxomicin.

Authors:  Sreenivas Katukojvala; Kristin N Barlett; Stephen D Lotesta; Lawrence J Williams
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

8.  Rhodium(II)-catalyzed aziridination of allyl-substituted sulfonamides and carbamates.

Authors:  Albert Padwa; Andrew C Flick; Carolyn A Leverett; Thomas Stengel
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

Review 9.  Aziridines: epoxides' ugly cousins?

Authors:  J B Sweeney
Journal:  Chem Soc Rev       Date:  2002-09       Impact factor: 54.564

Review 10.  Recent developments in allene-based synthetic methods.

Authors:  Hiyun Kim; Lawrence J Williams
Journal:  Curr Opin Drug Discov Devel       Date:  2008-11
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  17 in total

1.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

2.  Synthesis of 1,3-diaminated stereotriads via rearrangement of 1,4-diazaspiro[2.2]pentanes.

Authors:  Cale D Weatherly; Jared W Rigoli; Jennifer M Schomaker
Journal:  Org Lett       Date:  2012-03-20       Impact factor: 6.005

3.  Modular functionalization of allenes to aminated stereotriads.

Authors:  Christopher S Adams; Luke A Boralsky; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-06-20       Impact factor: 15.419

4.  A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines.

Authors:  Steven C Schmid; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-01       Impact factor: 15.336

5.  Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Authors:  Hillary J Dequina; Jennifer M Schomaker
Journal:  Trends Chem       Date:  2020-09-02

6.  Oxidative allene amination for the synthesis of azetidin-3-ones.

Authors:  Eileen G Burke; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-19       Impact factor: 15.336

7.  α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation.

Authors:  Josephine Eshon; Floriana Foarta; Clark R Landis; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2018-08-17       Impact factor: 4.354

8.  Allene Trifunctionalization via Amidyl Radical Cyclization and TEMPO Trapping.

Authors:  Robert M Ward; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2021-06-14       Impact factor: 4.354

Review 9.  Strategies for the Syntheses of Pactamycin and Jogyamycin.

Authors:  Nels C Gerstner; Kate A Nicastri; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-18       Impact factor: 15.336

10.  Chemoselective allene aziridination via Ag(I) catalysis.

Authors:  Jared W Rigoli; Cale D Weatherly; Brian T Vo; Samuel Neale; Alan R Meis; Jennifer M Schomaker
Journal:  Org Lett       Date:  2012-12-24       Impact factor: 6.005

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