Iridium-mediated β-deuteration of enones

被引:7
作者
Gibson, JS [1 ]
Herbert, JM [1 ]
机构
[1] Sanofi Synthelabo Res, Isotope Chem & Metab Synth Dept, Alnwick NE66 2JH, Northd, England
关键词
iridium complexes; isotope exchange; vinylic deuteration; orthodeuteration; H-2]-SR46349;
D O I
10.1002/jlcr.694
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Exposure of captodative enone systems to deuterium in the presence of Crabtree's catalyst (1) results in deuteration at the vinylic site beta- to the ketone carbonyl, as well as at any accessible ortho-position. beta-exchange is also observed during the reduction of ethyl cinnamate (3) catalyzed by 1. Copyright (C) 2003 John Wiley Sons, Ltd.
引用
收藏
页码:531 / 537
页数:7
相关论文
共 12 条
[1]   FACILE REVERSIBLE METALATION IN AN AGOSTIC COMPLEX AND HYDROGENOLYSIS OF A METAL ARYL COMPLEX VIA A DIHYDROGEN COMPLEX [J].
ALBENIZ, AC ;
SCHULTE, G ;
CRABTREE, RH .
ORGANOMETALLICS, 1992, 11 (01) :242-249
[2]  
CONGY C, CHEM ABS 230962, V113
[3]  
CONGY C, 1990, Patent No. 373998
[4]  
CROSS PWC, UNPUB TETRAHEDRON
[5]   The scope and limitations of deuteration mediated by Crabtree's catalyst [J].
Ellames, GJ ;
Gibson, JS ;
Herbert, JM ;
McNeill, AH .
TETRAHEDRON, 2001, 57 (46) :9487-9497
[6]  
HEYS JR, 1992, J CHEM SOC CHEM COMM, P680
[7]   ALIPHATIC VERSUS AROMATIC C-H ACTIVATION AND THE X-RAY CRYSTAL-STRUCTURE OF [IRH(H2O)(7,8-BENZOQUINOLINATO)(PPH3)2]SBF6 [J].
LAVIN, M ;
HOLT, EM ;
CRABTREE, RH .
ORGANOMETALLICS, 1989, 8 (01) :99-104
[8]   Reversible α-elimination in the conversion of N-CH3 to N-CH=Ir by double C-H activation [J].
Lee, DH ;
Chen, JY ;
Faller, JW ;
Crabtree, RH .
CHEMICAL COMMUNICATIONS, 2001, (02) :213-214
[9]  
RINALDICARMONA M, 1992, J PHARMACOL EXP THER, V262, P759
[10]   A CONVENIENT ALTERNATIVE ROUTE TO BETA-AMINOKETONES [J].
SANMARTIN, R ;
DEMARIGORTA, EM ;
DOMINGUEZ, E .
TETRAHEDRON, 1994, 50 (07) :2255-2264