Letters in Organic Chemistry ( IF 0.7 ) Pub Date : 2020-08-31 , DOI: 10.2174/1570178617666200225104238 Ismail E. Ismailov 1 , Ivaylo K. Ivanov 1 , Valerij Ch. Christov 1
This manuscript focuses on the reactions of 4-phosphorylated 5-hydroxyhexa-2,3-dienoates with protected or unprotected hydroxy groups involving 5-endo-trig cyclizations. Reactions with electrophiles result in mixtures of the 2,5-dihydro-1,2-oxaphosphole-5-carboxylates and the 5-phosphorylfuran- 2(5H)-ones by competitive electrophilic cyclization due to the neighboring phosphonate (phosphine oxide) and the carboxylate groups participation. 4-Phosphorylated 5-hydroxyhexa-2,3-dienoates were smoothly transformed into the corresponding 4-phosphoryl-2,5-dihydrofuran-2-carboxylates by using 5 mol % of a silver salt as a catalyst in the 5-endo-trig cycloisomerization reaction.
中文翻译:
三官能化的烯。第四部分 4-磷酸化5-羟基己二2,3-二烯酸酯的环化反应
该手稿着重于4-磷酸化的5-羟基己2,3-二烯酸酯与受保护或不受保护的羟基的反应,涉及5-内-trig环化。与亲电试剂的反应通过竞争性亲电环化反应生成2,5-二氢-1,2-氧杂磷酰基5-羧酸酯和5-磷酸基呋喃-2(5H)-酮的混合物,这是由于相邻的膦酸酯(氧化膦)和羧酸酯基团的参与。通过使用5-mol-trig中的5 mol%的银盐作为催化剂,将4-磷酸化的5-hydroxyhexa-2,3-dinoates平稳地转化为相应的4-phosphoryl-2,5-dihydrofuran-2-羧酸盐环异构化反应。