57210-37-4Relevant articles and documents
Vinyl-allenes as dienes in the Lewis acid-mediated hetero Diels-Alder reaction with aldehydes
Regas,Afonso,Galindo,Palenzuela
, p. 6781 - 6784 (2000)
The Lewis acid-mediated, hetero Diels-Alder reaction of a vinyl-allene system with aldehydes as heterodienophiles has been carried out. In the cases studied, only two cycloadducts have been obtained, which correspond to the endo (major compound) and exo (minor compound) approach of the aldehyde through the less hindered face of the dienic system. (C) 2000 Elsevier Science Ltd.
Synthesis of Highly Substituted Pyridines via [4 + 2] Cycloadditions of Vinylallenes and Sulfonyl Cyanides
Bartko, Samuel G.,Hamzik, Phillip J.,Espindola, Leandro,Gomez, Christian,Danheiser, Rick L.
supporting information, p. 548 - 563 (2019/12/27)
A convergent strategy for the synthesis of multisubstituted pyridines is described. Vinylallenes combine with commercially available arylsulfonyl cyanides in Diels-Alder cycloadditions to generate isopyridine cycloadducts that are converted to pyridines upon further heating or addition of a base. The 2-sulfonylpyridine products undergo nucleophilic aromatic substitution reactions with oxygen and carbon nucleophiles to provide access to a variety of highly substituted pyridines.
Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels–Alder reaction: Total synthesis of (?)-himbacine
Sugiyama, Koji,Kawanishi, Shinji,Oki, Yasuhiro,Kamiya, Marin,Hanada, Ryosuke,Egi, Masahiro,Akai, Shuji
, p. 1378 - 1386 (2017/10/06)
One-pot sequential reactions using the acyl moieties installed by enzymatic dynamic kinetic resolution of alcohols have been little investigated. In this work, the acryloyl moiety installed via the lipase/oxovanadium combo-catalyzed dynamic kinetic resolution of a racemic dienol [4-(cyclohex-1-en-1-yl)but-3-en-2-ol or 1-(cyclohex-1-en-1-yl)but-2-en-1-ol] with a (Z)-3-(phenylsulfonyl)acrylate underwent an intramolecular Diels–Alder reaction in a one-pot procedure to produce an optically active naphtho[2,3-c]furan-1(3H)-one derivative (98% ee). This method was successfully applied to the asymmetric total synthesis of (?)-himbacine.