Highly Diastereoselective Synthesis of Medium-Sized Carbocycle-Fused Piperidines via Sequential Hydride Shift Triggered Double C(sp3)–H Bond Functionalization

Miyabi Kataoka; Yuna Otawa; Natsuki Ido; Keiji Mori

doi:10.1021/acs.orglett.9b03498

Highly Diastereoselective Synthesis of Medium-Sized Carbocycle-Fused Piperidines via Sequential Hydride Shift Triggered Double C(sp3)–H Bond Functionalization

Organic Letters ◽

10.1021/acs.orglett.9b03498 ◽

2019 ◽

Vol 21 (23) ◽

pp. 9334-9338 ◽

Cited By ~ 9

Author(s):

Miyabi Kataoka ◽

Yuna Otawa ◽

Natsuki Ido ◽

Keiji Mori

Keyword(s):

Diastereoselective Synthesis ◽

Bond Functionalization ◽

Hydride Shift

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Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization

Chemical Science ◽

10.1039/c8sc02103a ◽

2018 ◽

Vol 9 (37) ◽

pp. 7327-7331 ◽

Cited By ~ 24

Author(s):

Keiji Mori ◽

Nobuaki Umehara ◽

Takahiko Akiyama

Keyword(s):

Bronsted Acid ◽

Brønsted Acid ◽

Diastereoselective Synthesis ◽

Bond Functionalization ◽

Hydride Shift ◽

Brönsted Acid ◽

Acid Catalyzed

Highly diastereoselective synthesis of tricyclic fused-pyrans was achieved by Brønsted acid catalyzed double C(sp3)–H bond functionalization.

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ChemInform Abstract: Expeditious Synthesis of 1-Aminoindane Derivatives Achieved by [1,4]-Hydride Shift Mediated C(sp3)-H Bond Functionalization.

ChemInform ◽

10.1002/chin.201435113 ◽

2014 ◽

Vol 45 (35) ◽

pp. no-no

Author(s):

Keiji Mori ◽

Kazuki Kurihara ◽

Takahiko Akiyama

Keyword(s):

Bond Functionalization ◽

Hydride Shift

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Rapid Access to 3-Aryltetralin Skeleton via C(sp3)–H Bond Functionalization: Investigation on the Substituent Effect of Aromatic Ring Adjacent to C–H Bond in Hydride Shift/Cyclization Sequence

Chemistry Letters ◽

10.1246/cl.2011.1386 ◽

2011 ◽

Vol 40 (12) ◽

pp. 1386-1388 ◽

Cited By ~ 36

Author(s):

Keiji Mori ◽

Shosaku Sueoka ◽

Takahiko Akiyama

Keyword(s):

Aromatic Ring ◽

Substituent Effect ◽

Bond Functionalization ◽

Rapid Access ◽

Hydride Shift

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Expeditious synthesis of 1-aminoindane derivatives achieved by [1,4]-hydride shift mediated C(sp3)–H bond functionalization

Chemical Communications ◽

10.1039/c4cc00894d ◽

2014 ◽

Vol 50 (28) ◽

pp. 3729 ◽

Cited By ~ 34

Author(s):

Keiji Mori ◽

Kazuki Kurihara ◽

Takahiko Akiyama

Keyword(s):

Bond Functionalization ◽

Hydride Shift

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C–H Bond Functionalization via [1,5]-Hydride Shift/Cyclization Sequence: Approach to Spiroindolenines

The Journal of Organic Chemistry ◽

10.1021/jo5026817 ◽

2015 ◽

Vol 80 (2) ◽

pp. 1155-1162 ◽

Cited By ~ 36

Author(s):

Peng-Fei Wang ◽

Chun-Huan Jiang ◽

Xiaoan Wen ◽

Qing-Long Xu ◽

Hongbin Sun

Keyword(s):

Bond Functionalization ◽

Hydride Shift

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Highly Diastereoselective Synthesis of Tetralin-fused Spirooxindoles via Lewis Acid-catalyzed C(sp3)–H Bond Functionalization

Chemistry Letters ◽

10.1246/cl.180275 ◽

2018 ◽

Vol 47 (7) ◽

pp. 868-871 ◽

Cited By ~ 10

Author(s):

Mizuki Machida ◽

Keiji Mori

Keyword(s):

Lewis Acid ◽

Diastereoselective Synthesis ◽

Bond Functionalization ◽

Acid Catalyzed

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Diastereoselective Spirocyclization via Intramolecular C( sp 3 )−H Bond Functionalization Triggered by Sequential [1,5]‐Hydride Shift/Cyclization Process: Approach to Spiro‐tetrahydroquinolines

Advanced Synthesis & Catalysis ◽

10.1002/adsc.202001011 ◽

2020 ◽

Author(s):

Arup Bhowmik ◽

Sumit Das ◽

Writhabrata Sarkar ◽

K. M. Saidalavi ◽

Aniket Mishra ◽

...

Keyword(s):

Process Approach ◽

Bond Functionalization ◽

Hydride Shift ◽

Cyclization Process

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ChemInform Abstract: Rapid Access to 3-Aryltetralin Skeleton via C(sp3)-H Bond Functionalization: Investigation on the Substituent Effect of Aromatic Ring Adjacent to C-H Bond in Hydride Shift/Cyclization Sequence.

ChemInform ◽

10.1002/chin.201218100 ◽

2012 ◽

Vol 43 (18) ◽

pp. no-no

Author(s):

Keiji Mori ◽

Shosaku Sueoka ◽

Takahiko Akiyama

Keyword(s):

Aromatic Ring ◽

Substituent Effect ◽

Bond Functionalization ◽

Rapid Access ◽

Hydride Shift

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2,4-Dinitrophenol-Catalyzed α-C(sp3 )−H and C(sp)−H Bond Functionalization of Cyclic Amines and Alkynes: Highly Regio-/Diastereoselective Synthesis of α-Alkynyl-3-Amino-2-Oxindoles

Chemistry - A European Journal ◽

10.1002/chem.201601222 ◽

2016 ◽

Vol 22 (29) ◽

pp. 9948-9952 ◽

Cited By ~ 10

Author(s):

Mukesh Kumar ◽

Banni P. Kaur ◽

Swapandeep S Chimni

Keyword(s):

Diastereoselective Synthesis ◽

Bond Functionalization ◽

Cyclic Amines

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Hf(OTf)4-Catalyzed highly diastereoselective synthesis of 1,3-disubstituted tetralin derivatives via benzylic C(sp3)–H bond functionalization

Chemical Communications ◽

10.1039/c7cc01717k ◽

2017 ◽

Vol 53 (31) ◽

pp. 4319-4322 ◽

Cited By ~ 24

Author(s):

Taira Yoshida ◽

Keiji Mori

Keyword(s):

Diastereoselective Synthesis ◽

Bond Functionalization

A highly diastereoselective synthesis of 1,3-disubstituted tetralin derivatives was achieved via Hf(OTf)4-catalyzed benzylic C(sp3)–H bond functionalization.

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