高等学校化学学报
高等學校化學學報
고등학교화학학보
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES
2009年
12期
2400-2403
,共4页
朱敏%李立%孙娜波%李赫
硃敏%李立%孫娜波%李赫
주민%리립%손나파%리혁
手性有机高价碘盐%苯基(苯乙炔基)(10)-樟脑磺酸碘盐%β-二羰基化合物不对称α-苯乙炔基化反应
手性有機高價碘鹽%苯基(苯乙炔基)(10)-樟腦磺痠碘鹽%β-二羰基化閤物不對稱α-苯乙炔基化反應
수성유궤고개전염%분기(분을결기)(10)-장뇌광산전염%β-이탄기화합물불대칭α-분을결기화반응
Chiral hypervalentiodonium salt%Phenyl (phenylethynyl) iodonium ( 10-camphorsulfonate )%Asymmetric α-phenylethynylation of β-dicarbonyl compound
通过苯乙炔和羟基(+)-10-樟脑磺酰氧基碘苯在氯仿溶剂中反应,合成出一个新的手性炔基芳基碘盐[苯基(苯乙炔基)(10)-樟脑磺酸碘盐].该手性碘盐与β-二羰基化合物的烯醇式负离子在温和条件下易于反应,产物具有中等e.e.值,为β-二羰基化合物在α位不对称引进苯乙炔基提供了一个简单方便的方法.
通過苯乙炔和羥基(+)-10-樟腦磺酰氧基碘苯在氯倣溶劑中反應,閤成齣一箇新的手性炔基芳基碘鹽[苯基(苯乙炔基)(10)-樟腦磺痠碘鹽].該手性碘鹽與β-二羰基化閤物的烯醇式負離子在溫和條件下易于反應,產物具有中等e.e.值,為β-二羰基化閤物在α位不對稱引進苯乙炔基提供瞭一箇簡單方便的方法.
통과분을결화간기(+)-10-장뇌광선양기전분재록방용제중반응,합성출일개신적수성결기방기전염[분기(분을결기)(10)-장뇌광산전염].해수성전염여β-이탄기화합물적희순식부리자재온화조건하역우반응,산물구유중등e.e.치,위β-이탄기화합물재α위불대칭인진분을결기제공료일개간단방편적방법.
A novel chiral alkynyliodonium salt, phenyl (phenylethynyl) iodonium (10-camphorsulfonate) was prepared by simply stirring of phenylacetylene with [hydroxyl-( (( + )-10-camphorsulfonyl)oxy)iodo] benzene in CHCl_3 overnight at room temperature. The asymmetric reaction with enolate anions of β-dicarbonyl compounds was studied in t-BuOH at room temperature, which gave good yields of β-phenylethynylated products with moderate values of e. e. value. The method for asymmetric direct α-phenylethynylation of β-dicarbonyl compounds was first reported, which had some advantages such as mild reaction conditions, simple procedure and with moderate values of e. e. value. Furthermore, the scope of hypervalent iodine compounds in asymmetric organic synthesis could be extended.