Highly enantioselective synthesis of cyclopropylphosphonates catalyzed by chiral ruthenium porphyrins

被引:64
作者
Ferrand, Y [1 ]
Le Maux, P [1 ]
Simonneaux, G [1 ]
机构
[1] Univ Rennes 1, Inst Chim, Lab Chim Organomet & Biol, UMR 6509, F-35042 Rennes, France
关键词
D O I
10.1021/ol048567y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric addition of diisopropyl diazomethylphosphonate to styrene derivatives was carried out by using chiral ruthenium porphyrins as catalysts. The reaction proceeded under mild conditions and gave trans-cyclopropylphosphonates with good yields and high ee's (up to 92%). A progressive increase for stereochemical effectiveness exists between enantiomeric excess and the number of chiral goups linked to ruthenium porphyrins.
引用
收藏
页码:3211 / 3214
页数:4
相关论文
共 24 条
[1]   Electronically tuned chiral ruthenium porphyrins: Extremely stable and selective catalysts for asymmetric epoxidation and cyclopropanation [J].
Berkessel, A ;
Kaiser, P ;
Lex, J .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (19) :4746-4756
[2]   Asymmetric inter- and intramolecular cyclopropanation of alkenes catalyzed by chiral ruthenium porphyrins. Synthesis and crystal structure of a chiral metalloporphyrin carbene complex [J].
Che, CM ;
Huang, JS ;
Lee, FW ;
Li, Y ;
Lai, TS ;
Kwong, HL ;
Teng, PF ;
Lee, WS ;
Lo, WC ;
Peng, SM ;
Zhou, ZY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4119-4129
[3]   Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles [J].
Cheung, WH ;
Zheng, SL ;
Yu, WY ;
Zhou, GC ;
Che, CM .
ORGANIC LETTERS, 2003, 5 (14) :2535-2538
[4]   SYNTHESIS AND BIOLOGICAL EVALUATION OF CYCLOPROPYL ANALOGS OF 2-AMINO-5-PHOSPHONOPENTANOIC ACID [J].
DAPPEN, MS ;
PELLICCIARI, R ;
NATALINI, B ;
MONAHAN, JB ;
CHIORRI, C ;
CORDI, AA .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :161-168
[5]   Enantioselective synthesis of cyclopropylphosphonates containing quaternary stereocenters using a D2-symmetric chiral catalyst Rh2(S-biTISP)2 [J].
Davies, HML ;
Lee, GH .
ORGANIC LETTERS, 2004, 6 (13) :2117-2120
[6]   Electrosynthesis of α-arylated β-substituted cyclopropylphosphonates.: Synthesis of a phosphonic analogue of minalcipran [J].
Duquenne, C ;
Goumain, S ;
Jubault, P ;
Feasson, C ;
Quirion, JC .
ORGANIC LETTERS, 2000, 2 (04) :453-455
[7]   1-AMINOCYCLOPROPANEPHOSPHONATE - TIME-DEPENDENT INACTIVATION OF 1-AMINOCYCLOPROPANECARBOXYLATE DEAMINASE AND BACILLUS-STEAROTHERMOPHILUS ALANINE RACEMASE BY SLOW DISSOCIATION BEHAVIOR [J].
ERION, MD ;
WALSH, CT .
BIOCHEMISTRY, 1987, 26 (12) :3417-3425
[8]   Asymmetric cyclopropanation of alkenes and diazocarbonyl insertion into S-H bonds catalyzed by a chiral porphyrin Ru(II) complex. [J].
Galardon, E ;
Roué, S ;
Le Maux, P ;
Simonneaux, G .
TETRAHEDRON LETTERS, 1998, 39 (16) :2333-2334
[9]   The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides [J].
Hah, JH ;
Gil, JM ;
Oh, DY .
TETRAHEDRON LETTERS, 1999, 40 (47) :8235-8238
[10]   CATALYTIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED ALKENES USING THE 1ST D4-SYMMETRICAL METALLOTETRAPHENYLPORPHYRIN [J].
HALTERMAN, RL ;
JAN, ST .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5253-5254