Dirhodium tetraprolinate-catalyzed asymmetric cycloproplanations with high turnover numbers

被引：67

作者：

Davies, HML ^{[1
]}

Venkataramani, C ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 09期

关键词：

D O I：

10.1021/ol034002a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic The bridged dirhodium tetraprolinate Rh-2(S-biTISP)(2) (2) catalyzes the asymmetric cyclopropanation reaction between methyl phenyldiazoacetate and styrene at room temperature with high turnover number (92 000) and turnover frequency (4000 per h).

引用

页码：1403 / 1406

页数：4

共 28 条

[1] Asymmetric inter- and intramolecular cyclopropanation of alkenes catalyzed by chiral ruthenium porphyrins. Synthesis and crystal structure of a chiral metalloporphyrin carbene complex
Che, CM
Huang, JS
Lee, FW
Li, Y
Lai, TS
Kwong, HL
Teng, PF
Lee, WS
Lo, WC
Peng, SM
Zhou, ZY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) : 4119 - 4129
[2] A CATALYTIC ENANTIOSELECTIVE SYNTHETIC ROUTE TO THE IMPORTANT ANTIDEPRESSANT SERTRALINE
COREY, EJ
GANT, TG
[J]. TETRAHEDRON LETTERS, 1994, 35 (30) : 5373 - 5376
[3] Davies H. M. L., 2001, ORG REACTIONS, V59, P1
[4] Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen
Davies, HML
Nagashima, T
Klino, JL
[J]. ORGANIC LETTERS, 2000, 2 (06) : 823 - 826
[5] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid
Davies, HML
Bruzinski, PR
Lake, DH
Kong, N
Fall, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) : 6897 - 6907
[6] Catalytic asymmetric C-H activation of sp3 hybridized C-H bonds by means of carbenoid C-H insertions:: applications in organic synthesis
Davies, HML
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 189 (01) : 125 - 135
[7] Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity
Davies, HML
Panaro, SA
[J]. TETRAHEDRON, 2000, 56 (28) : 4871 - 4880
[8] CONTROL OF CARBENOID REACTIVITY THROUGH NEIGHBORING GROUP PARTICIPATION
DAVIES, HML
MATASI, JJ
THORNLEY, C
[J]. TETRAHEDRON LETTERS, 1995, 36 (40) : 7205 - 7208
[9] ALPHA-HYDROXY ESTERS AS CHIRAL AUXILIARIES IN ASYMMETRIC CYCLOPROPANATIONS BY RHODIUM(II)-STABILIZED VINYLCARBENOIDS
DAVIES, HML
HUBY, NJS
CANTRELL, WR
OLIVE, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) : 9468 - 9479
[10] Tandem asymmetric cyclopropanation/cope rearrangement. A highly diastereoselective and enantioselective method for the construction of 1,4-cycloheptadienes
Davies, HML
Stafford, DG
Doan, BD
Houser, JH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) : 3326 - 3331

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