高压条件下丙二酸二烷基酯对β-芳基乙烯基磺酰氟的对映选择性加成反应
Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions.
作者信息
Kopyt Michał, Tryniszewski Michał, Barbasiewicz Michał, Kwiatkowski Piotr
机构信息
Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland.
Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland.
出版信息
Org Lett. 2023 Sep 22;25(37):6818-6822. doi: 10.1021/acs.orglett.3c02302. Epub 2023 Sep 1.
Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yields of up to 96% and enantioselectivities of up to 92%. Functionalization of the adducts via sulfur fluoride exchange (SuFEx) reaction and desulfonylative cyclization is demonstrated.
高压条件的应用能够实现丙二酸二烷基酯对β-芳基乙烯基磺酰氟的对映选择性迈克尔型加成反应。该反应在9千巴压力下用5摩尔%的叔氨基硫脲能高效催化。手性链烷磺酰氟的产率高达96%，对映选择性高达92%。还展示了通过硫氟交换（SuFEx）反应和脱磺酰环化对加合物进行官能团化。
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