Oxidative Dearomatization and Sigmatropic 1,3-Acyl Shift in Excited State: Aromatics to Embellished cis-Hydrindanes

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1633-1642
Author(s):  
Vishwakarma Singh ◽  
Raghaba Sahu
Keyword(s):  
Excited State ◽  
Ring Expansion ◽  
Synthetic Route ◽  
Oxidative Dearomatization ◽  
Key Features

A stereoselective synthetic route to embellished cis-hydrindanes from simple aromatic precursors is described. Oxidative dearomatization, ring expansion, and photochemical 1,3-acyl shift are the key features of our approach. Oxidative dearomatization of o-(hydroxymethyl)phenols followed by π4s + π2s cycloaddition furnishes bicyclo[2.2.2]octanes with contiguous keto epoxide groups, which upon ring expansion lead to bicyclo[3.2.2]nonanes endowed with a β,γ-enone chromophore. Unbridging of bicyclo[3.2.2]nonanes upon singlet excitation furnishes embellished cis-hydrindanes.

Magnesium Tetra(phenylethynyl)porphyrin: Stepwise Synthetic Route, Crystal Structures, and Longer Singlet Excited-State Lifetime than Zinc Congener

2018 ◽  
Vol 13 (20) ◽  
pp. 3032-3039 ◽  
Author(s):  
Takafumi Nakagawa ◽  
Huan Wang ◽  
Anna Zieleniewska ◽  
Hiroshi Okada ◽  
Shinobu Aoyagi ◽  
...  
Keyword(s):  
Excited State ◽  
Crystal Structures ◽  
Singlet Excited State ◽  
Synthetic Route ◽  
Excited State Lifetime

scholarly journals New Syntheses and Ring Expansion Reactions of Cyclobutenimines

2010 ◽  
Vol 63 (12) ◽  
pp. 1656 ◽  
Author(s):  
Ernst Schaumann ◽  
Gerrit Oppermann ◽  
Michael Stranberg ◽  
Harold W. Moore
Keyword(s):  
Carbonyl Group ◽  
Ring Expansion ◽  
Synthetic Route ◽  
Tertiary Alcohols ◽  
Ring Enlargement ◽  
Alkyl Derivatives

Two routes are reported for the synthesis of iminocyclobutenones having N-(het)aryl substitution: an addition/substitution sequence starting with cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein’s reagent and subsequent deprotonation under non-hydrolytic conditions. Lithium organyls were found to add to the remaining carbonyl group. The resulting tertiary alcohols undergo ring enlargement on heating in xylene to give 4-aminophenols, 4-amino-1-naphthols, or cyclopenta-annulated quinolines from 4-vinyl, 4-aryl, and 4-alkynyl derivatives, respectively.

scholarly journals Synthesis of Benzannulated Medium-Ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction

2018 ◽  
Vol 24 (50) ◽  
pp. 13063-13063 ◽  
Author(s):  
Tezcan Guney ◽  
Todd A. Wenderski ◽  
Matthew W. Boudreau ◽  
Derek S. Tan
Keyword(s):  
Ring Expansion ◽  
Oxidative Dearomatization ◽  
Ring Expansion Reaction ◽  
Medium Ring

scholarly journals Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction

2018 ◽  
Vol 24 (50) ◽  
pp. 13150-13157 ◽  
Author(s):  
Tezcan Guney ◽  
Todd A. Wenderski ◽  
Matthew W. Boudreau ◽  
Derek S. Tan
Keyword(s):  
Ring Expansion ◽  
Oxidative Dearomatization ◽  
Ring Expansion Reaction ◽  
Medium Ring

Total Synthesis of Citreochlorol Monochloro Analogs via a Catalytically Enantioselective Carbonyl Allylation

Synthesis ◽  
2021 ◽  
Author(s):  
Cheng-Kun Lin ◽  
Bing-Han Hsieh ◽  
Chun-Fu Wu
Keyword(s):  
Secondary Metabolites ◽  
Total Synthesis ◽  
Synthetic Route ◽  
Epoxide Opening ◽  
Key Features ◽  
Carbonyl Allylation

An efficient synthetic route to citreochlorol analogs, halogenated polyketide secondary metabolites, is described. The key features are Krische's enantioselective carbonyl allylation, IBr-promoted cyclization, and regioselective epoxide opening. The importance of the route lies in the access of the versatile epoxy ether 14, which opens access to the citreochlorol monochloro derivatives 5 and 6.

Ring Expansion of 2‐(α‐Hydroxyalkyl)azetidines: A Synthetic Route to Functionalized Pyrrolidines

2008 ◽  
Vol 2008 (19) ◽  
pp. 3286-3297 ◽  
Author(s):  
François Durrat ◽  
Monica Vargas Sanchez ◽  
François Couty ◽  
Gwilherm Evano ◽  
Jérôme Marrot
Keyword(s):  
Ring Expansion ◽  
Synthetic Route
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