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Synthesis of Functionalized 3,4‐Dihydropyrans via Rearrangement of the Products of a One‐Pot Diastereoselective Assembly of Ketones and Acetylene
Author(s) -
Schmidt Elena Yu.,
Trofimov Boris A.,
Zoridezhda V.,
Mikhaleva Albina I.,
Ushakov Igor A.,
Skital'tseva Elena V.,
Kazheva Olga N.,
Alexandrov Grigorii G.,
Dyachenko Oleg A.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001229
Subject(s) - chemistry , acetylene , methylene , pheromone , cope rearrangement , organic chemistry , carroll rearrangement , one pot synthesis , catalysis , stereochemistry , sigmatropic reaction , botany , biology
The products of the one‐pot assembly of ketones and acetylene, 7‐methylene‐6,8‐dioxabicyclo[3.2.1]octanes, congeners of an insect pheromone frontalin, undergo an acid‐catalyzed rearrangement to diastereomerically pure 2‐acetyl‐3,4‐dihydropyrans in excellent yields. The synthesis is realizable in a one‐pot manner procedure directly from ketones and acetylene.