Tandem Michael Addition?Carbene Insertion Reaction of 1-Alkynyl(aryl)(tetrafluoroborato)-?3-bromanes: 1-(Phenylsulfonyl)- and 1-(Trifluoromethylsulfonyl)cyclopentene Annulation.

Masahito Ochiai; Norihiro Tada; Yoshio Nishi; Kentaro Murai

doi:10.1002/chin.200518036

Tandem Michael Addition?Carbene Insertion Reaction of 1-Alkynyl(aryl)(tetrafluoroborato)-?3-bromanes: 1-(Phenylsulfonyl)- and 1-(Trifluoromethylsulfonyl)cyclopentene Annulation.

ChemInform ◽

10.1002/chin.200518036 ◽

2005 ◽

Vol 36 (18) ◽

Author(s):

Masahito Ochiai ◽

Norihiro Tada ◽

Yoshio Nishi ◽

Kentaro Murai

Keyword(s):

Michael Addition ◽

Insertion Reaction ◽

Carbene Insertion

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A new method for the synthesis of cyclopentenones via the tandem Michael addition-carbene insertion reaction of .beta.-ketoethynyl(phenyl)iodonium salts

Journal of the American Chemical Society ◽

10.1021/ja00080a011 ◽

1994 ◽

Vol 116 (1) ◽

pp. 93-98 ◽

Cited By ~ 55

Author(s):

Bobby L. Williamson ◽

Rik R. Tykwinski ◽

Peter J. Stang

Keyword(s):

Michael Addition ◽

New Method ◽

Insertion Reaction ◽

Iodonium Salts ◽

Carbene Insertion

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ChemInform Abstract: A New Method for the Synthesis of Cyclopentenones via the Tandem Michael Addition-Carbene Insertion Reaction of β-Ketoethynyl( phenyl)iodonium Salts.

ChemInform ◽

10.1002/chin.199418044 ◽

2010 ◽

Vol 25 (18) ◽

pp. no-no

Author(s):

B. L. WILLIAMSON ◽

R. R. TYKWINSKI ◽

P. J. STANG

Keyword(s):

Michael Addition ◽

New Method ◽

Insertion Reaction ◽

Iodonium Salts ◽

Carbene Insertion

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Tandem Michael addition–carbene insertion reaction of 1-alkynyl(aryl)(tetrafluoroborato)-λ3-bromanes: 1-(phenylsulfonyl)- and 1-(trifluoromethylsulfonyl)cyclopentene annulation

Chemical Communications ◽

10.1039/b410830b ◽

2004 ◽

pp. 2894-2895 ◽

Cited By ~ 15

Author(s):

Masahito Ochiai ◽

Norihiro Tada ◽

Yoshio Nishi ◽

Kentaro Murai

Keyword(s):

Michael Addition ◽

Insertion Reaction ◽

Carbene Insertion

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ChemInform Abstract: Aminopalladation-Triggered Carbene Insertion Reaction: Synthesis of 2-(1H-Indol-3-yl)acetates.

ChemInform ◽

10.1002/chin.201530165 ◽

2015 ◽

Vol 46 (30) ◽

pp. no-no

Author(s):

Ziwei Hu ◽

Shuang Luo ◽

Qiang Zhu

Keyword(s):

Insertion Reaction ◽

Reaction Synthesis ◽

Carbene Insertion

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Organocatalytic Asymmetric Synthesis of α-Amino Esters from Sulfoxonium Ylides

Chemical Science ◽

10.1039/d1sc02439f ◽

2021 ◽

Author(s):

Wengang Guo ◽

Hai Huang ◽

Jianwei Sun

Keyword(s):

Asymmetric Synthesis ◽

Insertion Reaction ◽

Metal Catalyst ◽

Insertion Reactions ◽

Amino Esters ◽

Carbene Insertion

Described here is the first organocatalytic asymmetric N−H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions....

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ChemInform Abstract: NOVEL CYCLOBUTANONE-FORMING CARBENE INSERTION REACTION. TETRACYCLO(7.3.1.02,5.05,10)TRIDECAN-4-ONE FROM 1-(TRICYCLO-(5.3.1.03,8)UNDEC-3-YL)-2-DIAZOETHAN-1-ONE

Chemischer Informationsdienst ◽

10.1002/chin.197606171 ◽

1976 ◽

Vol 7 (6) ◽

pp. no-no

Author(s):

N. TAKAISHI ◽

Y. FUJIKURA ◽

Y. INAMOTO ◽

H. IKEDA

Keyword(s):

Insertion Reaction ◽

Carbene Insertion

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A stereocontrolled, enantiomerically specific total synthesis of thienamycin

Philosophical Transactions of the Royal Society of London Series B Biological Sciences ◽

10.1098/rstb.1980.0037 ◽

1980 ◽

Vol 289 (1036) ◽

pp. 191-195 ◽

Cited By ~ 7

Keyword(s):

Total Synthesis ◽

Aspartic Acid ◽

Ring System ◽

Insertion Reaction ◽

Carbene Insertion ◽

Metal Catalyzed

A versatile stereocontrolled total synthesis of thienamycin starting from L-aspartic acid is reported. Stereocontrol is achieved by potassium tri- sec -butylborohydride reduction of a thermodynamically formed 3α-acetylazetidinone intermediate. The key [3.2.0] bicyclic ring system is prepared by a metal catalyzed carbene insertion reaction.

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