Ring strain-dictated divergent fluorinating Prins cyclization or semipinacol rearrangement

2017 ◽  
Vol 15 (31) ◽  
pp. 6478-6482 ◽  
Author(s):  
Yi Liu ◽  
Ying-Yeung Yeung
Keyword(s):  
Prins Cyclization ◽  
Ring Strain ◽  
Semipinacol Rearrangement ◽  
Prins Cyclizations

We have developed ring-strain dictated divergent diastereoselective fluorinating Prins cyclizations or semipinacol rearrangements to access a range of tetrahydropyran derivatives.

A new strategy for synthesis of attached rings

2000 ◽  
Vol 78 (6) ◽  
pp. 732-738 ◽  
Author(s):  
Larry E Overman ◽  
Lewis D Pennington
Keyword(s):  
Prins Cyclization ◽  
Pinacol Rearrangement ◽  
Carbon Migration ◽  
New Strategy ◽  
Prins Cyclizations

The first investigation of the use of pinacol-terminated Prins cyclizations to form attached rings is reported. Treatment of triisopropylsilyl ethers of (Z)- or (E)-[2-(6,6-dimethoxyhexylidene)cyclohexanol with SnCl4 provides bicyclic products having attached rings. The approach is synthetically useful in the Z alkylidenecyclohexane series, proceeding selectively by a pathway involving carbon migration in the pinacol rearrangement step, to provide methoxy epimers of 1-(2-methoxycyclohexyl)cyclopentylcarboxaldehyde. Reaction of the corresponding E stereoisomer is more complex and yields a mixture of products resulting from both hydride and carbon migration in the pinacol rearrangement step.Key words: Prins cyclization, pinacol rearrangement, attached rings.

scholarly journals ZnAlMCM-41; a very ecofriendly and reusable solid acid catalyst for highly selective synthesis of 1, 3-dioxanes by Prins cyclization of olefins

2021 ◽  
Author(s):  
Manickam Selvaraj ◽  
Mohammed A. Assiri ◽  
Hari Singh ◽  
Jimmy Nelson Appaturi ◽  
Subrahmanyam Ch ◽  
...  
Keyword(s):  
Liquid Phase ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Selective Synthesis ◽  
Comparison Study ◽  
Catalytic Method ◽  
Prins Cyclization ◽  
Heterogeneous Catalytic

Prins cyclization of styrene (SE) with paraformaldehyde (PFCHO) was conducted with mesoporous ZnAlMCM-41 catalysts for synthesis of 4-phenyl-1,3-dioxane (4-PDO) under a liquid phase heterogeneous catalytic method. For comparison study, the...

Bis(perchlorocatecholato)silane and Heteroleptic Bidonors: Hidden Frustrated Lewis Pairs by Ring Strain

2021 ◽  
Author(s):  
Deborah Hartmann ◽  
Sven Braner ◽  
Lutz Greb
Keyword(s):  
Ammonia Borane ◽  
Frustrated Lewis Pairs ◽  
Ring Strain ◽  
Frustrated Lewis Pair ◽  
Lewis Pairs

Bis(perchlorocatecholato)silane and bidentate N,N- or N,P-heteroleptic donors form hexacoordinated complexes. Depending on the ring strain and hemilability in the adducts, Frustrated Lewis pair reactivity with aldehydes and catalytic ammonia borane...

scholarly journals Recent development and applications of semipinacol rearrangement reactions

2021 ◽  
Author(s):  
Xiao-Ming Zhang ◽  
Bao-Sheng Li ◽  
Shao-Hua Wang ◽  
Kun Zhang ◽  
Fu-Min Zhang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Carbon Formation ◽  
Semipinacol Rearrangement ◽  
Rearrangement Reactions

The recent development of semipinacol rearrangement is reviewed, highlighting its application in β-functionalized ketone synthesis, quaternary carbon formation and total synthesis.

scholarly journals Efficient Synthesis of Carbovir and Its Congenerviaπ-Allylpalladium Complex Fomation by Ring Strain-Assisted C−N Bond Cleavage

1998 ◽  
Vol 63 (6) ◽  
pp. 2052-2052
Author(s):  
Nobuya Katagiri ◽  
Masahiro Takebayashi ◽  
Chikara Kaneko ◽  
Kouichi Kanehira ◽  
Masahiro Torihara
Keyword(s):  
Bond Cleavage ◽  
Efficient Synthesis ◽  
Ring Strain

Trapping-Mediated Dissociative Chemisorption of Cycloalkanes on Ru(001) and Ir(111):  Influence of Ring Strain and Molecular Geometry on the Activation of C−C and C−H Bonds

2001 ◽  
Vol 123 (5) ◽  
pp. 929-940 ◽  
Author(s):  
Christopher J. Hagedorn ◽  
Michael J. Weiss ◽  
Tae Won Kim ◽  
W. Henry Weinberg
Keyword(s):  
Molecular Geometry ◽  
Dissociative Chemisorption ◽  
Ring Strain

scholarly journals The Silylalkyne-Prins Cyclization: Stereoselective Synthesis of Tetra- and Pentasubstituted Halodihydropyrans.

ChemInform ◽  
2006 ◽  
Vol 37 (34) ◽  
Author(s):  
Pedro O. Miranda ◽  
Miguel A. Ramirez ◽  
Victor S. Martin ◽  
Juan I. Padron
Keyword(s):  
Stereoselective Synthesis ◽  
Prins Cyclization

Delineating the possibilities for intramolecular interception of the squarate ester cascade through the use of metalated enecarbamates

2000 ◽  
Vol 78 (6) ◽  
pp. 689-696 ◽  
Author(s):  
Jinsung Tae ◽  
Leo A Paquette
Keyword(s):  
Ring Opening ◽  
Membered Ring ◽  
Sequential Treatment ◽  
Nucleophilic Attack ◽  
Ring Strain ◽  
Multistep Process

Highly functionalized and annulated 2,4-cyclooctadienones are formed in a stereoselective manner by sequential treatment of squarate esters with a lithiated enecarbamate (six-membered ring or larger) and a cycloalkenyl- or 1-alkenyllithium reagent. The mechanistic details of this multistep process are presented. Particular attention is drawn to the step that involves intramolecular nucleophilic attack by a proximal oxido anion at the carbamate carbonyl and results in redirection of the cascade. This step is thwarted when five-membered cyclic enecarbamates are employed because of the excessive buildup of ring strain in the associated transition state.Key words: squarate esters, enecarbamates, conrotatory ring opening, intramolecular acylation, alkenyllithium reagents.

ChemInform Abstract: A Cascade Aza-Cope/Aza-Prins Cyclization Leading to Piperidine Derivatives.

ChemInform ◽  
2015 ◽  
Vol 46 (31) ◽  
pp. no-no
Author(s):  
Jothi L. Nallasivam ◽  
Rodney A. Fernandes
Keyword(s):  
Prins Cyclization
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