Asymmetric catalytic C-H activation applied to the synthesis of syn-aldol products

被引：62

作者：

Davies, HML ^{[1
]}

Antoulinakis, EG ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 26期

关键词：

D O I：

10.1021/ol006671j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Rh-2(R-DOSP)(4)-catalyzed decomposition of methyl phenyldiazoacetate in the presence of tetraalkoxysilanes results in the asymmetric synthesis of syn-aldol products. This catalytic asymmetric intermolecular C-H activation proceeds by means of a rhodium-carbene-induced CH insertion.

引用

页码：4153 / 4156

页数：4

共 25 条

[1] AHN M, 1998, J CHEM SOC P1, V2, P185
[2] Enantioselective synthesis of D-threo-methylphenidate
Axten, JM
Ivy, R
Krim, L
Winkler, JD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) : 6511 - 6512
[3] CARREIRA EM, 1999, COMPREHENSIVE ASYMME, V3, P997
[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] Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran
Davies, HML
Hansen, T
Churchill, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) : 3063 - 3070
[6] NOVEL ENTRY TO THE TROPANE SYSTEM BY REACTION OF RHODIUM(II) ACETATE STABILIZED VINYLCARBENOIDS WITH PYRROLES
DAVIES, HML
YOUNG, WB
SMITH, HD
[J]. TETRAHEDRON LETTERS, 1989, 30 (35) : 4653 - 4656
[7] 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
[8] Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity
Davies, HML
Panaro, SA
[J]. TETRAHEDRON, 2000, 56 (28) : 4871 - 4880
[9] Asymmetric synthesis of cyclopentenes by [3+2] annulations between vinylcarbenoids and vinyl ethers
Davies, HML
Kong, N
Churchill, MR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) : 6586 - 6589
[10] Effect of catalyst on the diastereoselectivity of methyl phenyldiazoacetate cyclopropanations
Davies, HML
Rusiniak, L
[J]. TETRAHEDRON LETTERS, 1998, 39 (48) : 8811 - 8812

← 1 2 3 →