Literature DB >> 15137750

Enantioselective tandem O-nitroso Aldol/Michael reaction.

Yuhei Yamamoto1, Norie Momiyama, Hisashi Yamamoto.   

Abstract

This communication presents studies that illustrated nitroso Diels-Alder adduct has been obtained in uniformly high enantioselectivity via a tandem nitroso aldol/Michael reaction using an amine catalyst. The regiochemical outcome of this construction is documented to be the opposite to that of the normal nitroso aldol reaction, which has been determined by X-ray analysis. The reaction of the enone with silver-BINAP catalyst has also been investigated in conjunction with the control of regiochemistry in a stepwise process.

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Year:  2004        PMID: 15137750     DOI: 10.1021/ja049741g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

1.  Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors:  Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

2.  Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis.

Authors:  Norie Momiyama; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

3.  Continuous flow of nitroso Diels-Alder reaction.

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

4.  Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.

Authors:  Grant S Buchanan; Huifang Dai; Richard P Hsung; Aleksey I Gerasyuto; Casi M Scheinebeck
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

5.  Catalytic asymmetric nitroso-Diels-Alder reaction with acyclic dienes.

Authors:  Yuhei Yamamoto; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-04       Impact factor: 15.336

Review 6.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

7.  Organocatalytic Highly Enantioselective Tandem Michael-Knoevenagel Reaction for the Synthesis of Substituted Thiochromanes.

Authors:  Rajasekhar Dodda; Tanmay Mandal; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2008-03-17       Impact factor: 2.415

8.  NHC-catalyzed reactions of aryloxyacetaldehydes: a domino elimination/conjugate addition/acylation process for the synthesis of substituted coumarins.

Authors:  Eric M Phillips; Manabu Wadamoto; Howard S Roth; Andrew W Ott; Karl A Scheidt
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

9.  Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction.

Authors:  Rajasekhar Dodda; Joshua J Goldman; Tanmay Mandal; Cong-Gui Zhao; Grant A Broker; Edward R T Tiekink
Journal:  Adv Synth Catal       Date:  2008-02-26       Impact factor: 5.837

10.  Ten years of research in Chicago.

Authors:  Hisashi Yamamoto
Journal:  Tetrahedron       Date:  2013-06-10       Impact factor: 2.457

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