Mechanism of Mukaiyama−Michael Reaction of Ketene Silyl Acetal:  Electron Transfer or Nucleophilic Addition?

Junzo Otera; Yukihiro Fujita; Nobuyuki Sakuta; Morifumi Fujita; Shunichi Fukuzumi

doi:10.1021/jo9512968

Mechanism of Mukaiyama−Michael Reaction of Ketene Silyl Acetal: Electron Transfer or Nucleophilic Addition?

The Journal of Organic Chemistry ◽

10.1021/jo9512968 ◽

1996 ◽

Vol 61 (9) ◽

pp. 2951-2962 ◽

Cited By ~ 19

Author(s):

Junzo Otera ◽

Yukihiro Fujita ◽

Nobuyuki Sakuta ◽

Morifumi Fujita ◽

Shunichi Fukuzumi

Keyword(s):

Electron Transfer ◽

Nucleophilic Addition ◽

Michael Reaction

Download Full-text

Tandem Nucleophilic Addition−Intramolecular Aza-Michael Reaction: Facile Synthesis of Chiral Fluorinated Isoindolines

Organic Letters ◽

10.1021/ol102341n ◽

2010 ◽

Vol 12 (23) ◽

pp. 5494-5497 ◽

Cited By ~ 63

Author(s):

Santos Fustero ◽

Javier Moscardó ◽

María Sánchez-Roselló ◽

Elsa Rodríguez ◽

Pablo Barrio

Keyword(s):

Nucleophilic Addition ◽

Michael Reaction ◽

Facile Synthesis

Download Full-text

ChemInform Abstract: Preference of Electron Transfer to Nucleophilic Addition in Reactions of Ketene Silyl Acetals with Quinones and Catalysis of Magnesium Ion

ChemInform ◽

10.1002/chin.199631041 ◽

2010 ◽

Vol 27 (31) ◽

pp. no-no

Author(s):

M. FUJITA ◽

S. FUKUZUMI ◽

G. MATSUBAYASHI ◽

J. OTERA

Keyword(s):

Electron Transfer ◽

Nucleophilic Addition ◽

Magnesium Ion ◽

Silyl Acetals

Download Full-text

Direct Nucleophilic Addition versus a Single-Electron Transfer Pathway of σH Adduct Formation in Vicarious Nucleophilic Substitution of Hydrogen.

ChemInform ◽

10.1002/chin.200435070 ◽

2004 ◽

Vol 35 (35) ◽

Author(s):

Mieczyslaw Makosza ◽

Andrzej Kwast

Keyword(s):

Electron Transfer ◽

Nucleophilic Substitution ◽

Nucleophilic Addition ◽

Adduct Formation ◽

Single Electron ◽

Single Electron Transfer ◽

Nucleophilic Substitution Of Hydrogen ◽

Electron Transfer Pathway ◽

Vicarious Nucleophilic Substitution

Download Full-text

Electron transfer as a possible initial step in nucleophilic addition elimination reactions between (radical) anions and carbonyl compounds in the gas phase

Recueil des Travaux Chimiques des Pays-Bas ◽

10.1002/recl.19961150304 ◽

2010 ◽

Vol 115 (3) ◽

pp. 179-184 ◽

Cited By ~ 6

Author(s):

Paul O. Staneke ◽

Steen Ingemann ◽

Nico M. M. Nibbering

Keyword(s):

Electron Transfer ◽

Gas Phase ◽

Carbonyl Compounds ◽

Nucleophilic Addition ◽

Initial Step ◽

Radical Anions ◽

Elimination Reactions

Download Full-text

Intramolecular nucleophilic addition of silylenol ether to photosensitized electron transfer (PET) generated arene radical cations: A novel non-reagent based carboannulation reaction:

Tetrahedron Letters ◽

10.1016/0040-4039(93)88123-z ◽

1993 ◽

Vol 34 (41) ◽

pp. 6631-6634 ◽

Cited By ~ 16

Author(s):

Ganesh Pandey ◽

A. Krishna ◽

K. Girija ◽

M. Karthikeyan

Keyword(s):

Electron Transfer ◽

Nucleophilic Addition ◽

Radical Cations

Download Full-text

Competition between nucleophilic addition and electron-transfer process in the reaction of 9-diazo-10-anthrone with grignard reagents

Tetrahedron ◽

10.1016/0040-4020(96)00291-8 ◽

1996 ◽

Vol 52 (19) ◽

pp. 6795-6802 ◽

Cited By ~ 6

Author(s):

Paolo Bruni ◽

Patricia Carloni ◽

Carla Conti ◽

Elisabetta Giorgini ◽

Lucedio Greci ◽

...

Keyword(s):

Electron Transfer ◽

Transfer Process ◽

Nucleophilic Addition ◽

Grignard Reagents ◽

Electron Transfer Process

Download Full-text

ChemInform Abstract: Mukaiyama-Michael Reaction of Cyclic Ketene Silyl Acetals and Enones. Importance of Ring Flexibility in Electron Transfer Process.

ChemInform ◽

10.1002/chin.199726105 ◽

2010 ◽

Vol 28 (26) ◽

pp. no-no

Author(s):

Y. FUJITA ◽

S. FUKUZUMI ◽

J. OTERA

Keyword(s):

Electron Transfer ◽

Transfer Process ◽

Michael Reaction ◽

Electron Transfer Process ◽

Silyl Acetals

Download Full-text

Reaction of metallo-2-nitro-5,10,15,20-tetraphenylporphyrins with oxyanions. Temperature-dependent competition between nucleophilic addition and single-electron transfer processes

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19960001251 ◽

1996 ◽

pp. 1251 ◽

Cited By ~ 23

Author(s):

Maxwell J. Crossley ◽

Lionel G. King

Keyword(s):

Electron Transfer ◽

Nucleophilic Addition ◽

Single Electron ◽

Single Electron Transfer ◽

Temperature Dependent ◽

Transfer Processes ◽

Electron Transfer Processes

Download Full-text

ChemInform Abstract: Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans.

ChemInform ◽

10.1002/chin.201506181 ◽

2015 ◽

Vol 46 (6) ◽

pp. no-no

Author(s):

Santosh J. Gharpure ◽

J. V. K. Prasad ◽

Kalisankar Bera

Keyword(s):

Nucleophilic Addition ◽

Michael Reaction

Download Full-text

Preference of Electron Transfer to Nucleophilic Addition in Reactions of Ketene Silyl Acetals with Quinones and Catalysis of Magnesium Ion

Bulletin of the Chemical Society of Japan ◽

10.1246/bcsj.69.1107 ◽

1996 ◽

Vol 69 (4) ◽

pp. 1107-1116 ◽

Cited By ~ 9

Author(s):

Morifumi Fujita ◽

Shunichi Fukuzumi ◽

Gen-etsu Matsubayashi ◽

Junzo Otera

Keyword(s):

Electron Transfer ◽

Nucleophilic Addition ◽

Magnesium Ion ◽

Silyl Acetals

Download Full-text