Enantioselective synthesis of cyclopropylphosphonates containing quaternary stereocenters using a D2-symmetric chiral catalyst Rh2(S-biTISP)2

被引：45

作者：

Davies, HML ^{[1
]}

Lee, GH ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 13期

关键词：

D O I：

10.1021/ol049525c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh-2(SbiTISP)(2)-catalyzed reactions of dimethyl aryldiazomethylphosphonates generate donor/acceptor-substituted rhodium carbenoid intermediates capable of cyclopropanation of styrenes in high yields (85-96%), diastereoselectivity (greater than or equal to98% de), and enantioselectivity (76-92% ee).

引用

页码：2117 / 2120

页数：4

共 38 条

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[3] 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
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[4] Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates
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[5] Davies HML, 1999, ADV CYCLOAD, V5, P119
[6] Novel dirhodium tetraprolinate catalysts containing bridging prolinate ligands for asymmetric carbenoid reactions
Davies, HML
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[J]. TETRAHEDRON LETTERS, 1999, 40 (29) : 5287 - 5290
[7] Effect of carbenoid structure on the reactivity of rhodium-stabilized carbenoids
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[J]. TETRAHEDRON LETTERS, 1998, 39 (25) : 4417 - 4420
[8] DAVIES HML, 1999, EUR J ORG CHEM, V2459, P9
[9] ORGANIC PHOSPHORUS-COMPOUNDS .78. MANUFACTURE AND PROPERTIES OF N-PHOSPHONOMETHYLGLYCINE DERIVATIVES
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[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1984, 20 (03): : 313 - 321
[10] Electrosynthesis of α-arylated β-substituted cyclopropylphosphonates.: Synthesis of a phosphonic analogue of minalcipran
Duquenne, C
Goumain, S
Jubault, P
Feasson, C
Quirion, JC
[J]. ORGANIC LETTERS, 2000, 2 (04) : 453 - 455

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