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Pd(O) Promoted Transformation of 1,1‐Dialkoxycarbonyl‐2‐(1,3‐butadienyl)cyclopropanes into 2‐Ethenyl‐3‐cyclopentenes
Author(s) -
Morizawa Yoshitomi,
Oshima Koichiro,
Nozaki Hitosi
Publication year - 1984
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198400025
Subject(s) - chemistry , cyclopentene , yield (engineering) , medicinal chemistry , catalysis , transformation (genetics) , stereochemistry , organic chemistry , biochemistry , materials science , metallurgy , gene
1,3‐Butadienylcyclopropanes activated by two electron‐withdrawing groups ( 1 ) smoothly rearrange to vinylcyclopentene derivatives in the presence of a Pd(O) catalyst under mild conditions. For example, dimethyl 1,3‐butadienylcyclopropane‐1,1‐dicarboxylate 1a reacts with 3 mol% Pd(PPh 3 ) 4 in DMSO at 25–60 °C for 30 min to provide dimethyl 2‐ethenyl‐3‐cyclopentene‐1,1‐dicarboxylate 2a in 87% yield. Other data show that the new method is useful in the synthesis of cyclopentene derivatives including dolichodial and iridodiol.