Enantio- and diastereoselective cyclopropanation with tert-butyl α-diazopropionate catalyzed by dirhodium(II) tetrakis[N-tetrabromophthaloyl-(S)-tert-leucinate]

被引：35
作者：
Goto, Takayuki [1 ,2 ]
Takeda, Koji [1 ]
Anada, Masahiro [1 ]
Ando, Kaori [3 ]
Hashimoto, Shunichi [1 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Kyorin Pharmaceut Co Ltd, Dev Res Labs, Nogi, Tochigi 3290114, Japan
[3] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 32期
关键词：
Asymmetric catalysis; Cyclopropanation; Dirhodium(II) complex; alpha-Alkyl-alpha-diazoester; Carbene; C-H INSERTION; ASYMMETRIC INTRAMOLECULAR CYCLOPROPANATION; HIGHLY ENANTIOSELECTIVE CYCLOPROPANATION; METAL CARBENE TRANSFORMATIONS; CONTAINING NATURAL-PRODUCTS; CHIRAL RH(II) CATALYST; BETA-KETO SULFONES; INTERMOLECULAR CYCLOPROPANATION; STEREOSELECTIVE CYCLOPROPANATION; CYCLOPENTANE CONSTRUCTION;
D O I：
10.1016/j.tetlet.2011.06.008
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first successful example of a catalytic asymmetric cyclopropanation with alpha-diazopropionates is described. The cyclopropanation reaction of 1-aryl-substituted and related conjugated alkenes with tert-butyl (alpha-diazopropionate has been achieved by catalysis with dirhodium(II) tetrakis[N-tetrabromophthaloyl-(S)-tert-leucinate], Rh-2(S-TBPTTL)(4), providing the corresponding cyclopropane products containing a quarternary stereogenic center in good to high yields and with high diastereo- and enantioselectivities (trans:cis = 90:10 to >99:1, 81-93% ee). (C) 2011 Elsevier Ltd. All rights reserved.
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页码：4200 / 4203
页数：4
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