Mao Hui-Lin, Wang Yu-Xin, Wang Xue, Wang Hai-Ying, Hao Wen-Juan, Jiang Bo
School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, China.
Org Lett. 2023 Aug 18;25(32):5963-5968. doi: 10.1021/acs.orglett.3c02051. Epub 2023 Aug 4.
A palladium-catalyzed asymmetric annulative dearomatization of phenols with butene dicarbonate is reported, enabling twofold decarboxylative allylation to regioselectively produce a range of spirocyclohexadienones with 29-95% yields and 74-99% ee. A catalytic dearomative formal [4 + 2] cyclization of 1,1'-biphenyl-2,4'-diols delivered spiro[chromane-4,1'-cyclohexane]-2',5'-dien-4'-ones with high enantioselectivity, whereas enantioenriched spiro[cyclohexane-1,4'-quinoline]-2,5-dien-4-ones were generated starting from 2'-amino-[1,1'-biphenyl]-4-ols as 1,4-dinucleophiles.
报道了钯催化酚类与丁烯二碳酸酯的不对称环化脱芳反应，该反应通过双重脱羧烯丙基化反应，区域选择性地生成一系列螺环环己二烯酮，产率为29-95%，对映体过量值为74-99%。1,1'-联苯-2,4'-二醇的催化脱芳形式[4 + 2]环化反应以高对映选择性生成螺[色满-4,1'-环己烷]-2',5'-二烯-4'-酮，而对映体富集的螺[环己烷-1,4'-喹啉]-2,5-二烯-4-酮则由2'-氨基-[1,1'-联苯]-4-醇作为1,4-双亲核试剂生成。
