公开(公告)号：US20140296527A1

公开(公告)日：2014-10-02

申请号：US14346773

申请日：2012-09-28

Applicant: SYNGENTA PARTICIPATIONS AG

Inventor： Tomas Smejkal ,  Helmars Smits ,  Sebastian Volker Wendeborn ,  Guillaume Berthon ,  Jerome Yves Cassayre ,  Myriem El Qacemi

IPC: C07D453/04 ,  C07C255/41 ,  C07D207/08 ,  C07D307/46 ,  C07D207/325 ,  C07D207/12

CPC classification number: C07D453/04 ,  C07C253/10 ,  C07C253/30 ,  C07C255/40 ,  C07C255/41 ,  C07D207/08 ,  C07D207/12 ,  C07D207/267 ,  C07D207/325 ,  C07D207/333 ,  C07D207/40 ,  C07D307/46 ,  C07D409/12

Abstract: The present invention relates to processes for the enantio-selective preparation of spyrrolidine derivatives useful in the manufacture of pesticidally active compounds, as well as to intermediates in the processes. The processes include those comprising(a-i) reacting a compound of formula Ia wherein P is alkyl, aryl or heteroaryl, each optionally substituted, wherein the heteroaryl is connected at P via a ring carbon atom; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is aryl or heteroaryl, each optionally substituted; with a source of cyanide in the presence a chiral catalyst to give a compound of formula IIa wherein P, R1 and R2 are as defined for the compound of formula Ia; and (a-ii) oxidising the compound of formula IIa with a peroxy acid, or peroxide in the presence of an acid to give a compound of formula VI wherein R1 and R2 are as defined for the compound of formula Ia.

Abstract translation: 本发明涉及用于制备杀虫活性化合物的螺吡咯烷衍生物的对映选择性制备方法以及该方法中的中间体。 所述方法包括（a-i）使式Ia化合物（其中P为烷基，芳基或杂芳基）各自任意取代的化合物，其中杂芳基通过环碳原子在P连接; R1是氯二氟甲基或三氟甲基; R 2是芳基或杂芳基，各自任选被取代; 在存在手性催化剂的情况下产生氰化物源，得到式IIa化合物，其中P，R 1和R 2如对于式Ia化合物所定义; 和（a-ii）在酸存在下用过氧酸或过氧化物氧化式IIa化合物，得到式VI化合物，其中R 1和R 2如对于式Ia化合物所定义。