广东化工
廣東化工
엄동화공
GUANGDONG CHEMICAL INDUSTRY
2013年
7期
27-29
,共3页
何健兴%苏晶%林汉森*%李建组
何健興%囌晶%林漢森*%李建組
하건흥%소정%림한삼*%리건조
手性奎宁季铵盐%配体%不对称相转移催化%Darzens 反应
手性奎寧季銨鹽%配體%不對稱相轉移催化%Darzens 反應
수성규저계안염%배체%불대칭상전이최화%Darzens 반응
quinine quaternary ammonium salt%ligand%asymmetic phase-transfer catalytic%darzens reaction
文章以奎宁碱为母体,利用一系列卤代烃与奎宁碱发生季铵化反应,生成一系列手性奎宁季铵盐配体,所合成的配体结构均经1H-NMR、IR、MS 确证.并考察了该系列催化剂在不对称相转移催化2-氯代苯乙酮和苯甲醛的 Darzens 缩合反应中的催化性能,发现其手性催化性能跟取代基的立体位阻及电负性大小有关,其中由2-氟-4-溴苄基与奎宁形成的手性季铵盐不对称催化效果最好,所得缩合产物的 ee 值最高为46%.
文章以奎寧堿為母體,利用一繫列滷代烴與奎寧堿髮生季銨化反應,生成一繫列手性奎寧季銨鹽配體,所閤成的配體結構均經1H-NMR、IR、MS 確證.併攷察瞭該繫列催化劑在不對稱相轉移催化2-氯代苯乙酮和苯甲醛的 Darzens 縮閤反應中的催化性能,髮現其手性催化性能跟取代基的立體位阻及電負性大小有關,其中由2-氟-4-溴芐基與奎寧形成的手性季銨鹽不對稱催化效果最好,所得縮閤產物的 ee 值最高為46%.
문장이규저감위모체,이용일계렬서대경여규저감발생계안화반응,생성일계렬수성규저계안염배체,소합성적배체결구균경1H-NMR、IR、MS 학증.병고찰료해계렬최화제재불대칭상전이최화2-록대분을동화분갑철적 Darzens 축합반응중적최화성능,발현기수성최화성능근취대기적입체위조급전부성대소유관,기중유2-불-4-추변기여규저형성적수성계안염불대칭최화효과최호,소득축합산물적 ee 치최고위46%.
Through using a series of halogenated hydrocarbons and quinine alkaline quaternization reaction, a series of chiral quinine quaternary ammonium salt ligand were generated with quinine as base matrix and its synthesized ligand structure were confirmed by 1H-NMR, IR, MS. And catalytic performance of ligands in Darzens condensation reaction between 2- chloroacetophenone and benzaldehyde in the asymmetric catalytic condition was investigated, implying that the chiral catalytic properties were associated with the steric size of substituents. And the best enantioselectivity for 46 %was obtained.
