Ytterbium(III) triflate/TMSCI: Efficient catalyst for imino ene reaction

被引：119

作者：

Yamanaka, M ^{[1
]}

Nishida, A ^{[1
]}

Nakagawa, M ^{[1
]}

机构：

[1] Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol991260s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Ytterbium trifluoromethanesulfonate [Yb(OTf)(3)] catalyzed the imino ene reaction of N-tosyl aldimine with alpha-methylstyrene to give a homoallylamine in moderate yield. Furthermore, addition of a catalytic amount of chlorotrimethylsilane (TMSCI) dramatically enhanced the imino ene reaction.

引用

页码：159 / 161

页数：3

共 35 条

[1] ACHMATOWICZ O, 1976, J CHEM SOC CHEM COMM, P484
[2] A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2-c]quinolines
Batey, RA
Simoncic, PD
Lin, D
Smyj, RP
Lough, AJ
[J]. CHEMICAL COMMUNICATIONS, 1999, (07) : 651 - 652
[3] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
Bloch, R
[J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
[4] BORZILLERI RM, 1995, SYNTHESIS-STUTTGART, P347
[5] DRUY WJ, 1998, J AM CHEM SOC, V120, P11006
[6] C2-symmetric copper(II) complexes as chiral Lewis acids.: Enantioselective catalysis of the glyoxylate-ene reaction
Evans, DA
Burgey, CS
Paras, NA
Vojkovsky, T
Tregay, SW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) : 5824 - 5825
[7] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
Ferraris, D
Young, B
Dudding, T
Lectka, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4548 - 4549
[8] Mechanism of palladium complex-catalyzed enantioselective Mannich-type reaction: Characterization of a novel binuclear palladium enolate complex
Fujii, A
Hagiwara, E
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) : 5450 - 5458
[9] A new and highly efficient asymmetric route to cyclic α-amino phosphonates:: The first catalytic enantioselective hydrophosphonylation of cyclic imines catalyzed by chiral heterobimetallic lanthanoid complexes
Gröger, H
Saida, Y
Sasai, H
Yamaguchi, K
Martens, J
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) : 3089 - 3103
[10] Single crystal X-ray analyses of a series of hexamethylphosphoramide-coordinated complexes of rare earth triflates: Existence of tetrad effects in the coordinate bonds
Imamoto, T
Nishiura, M
Yamanoi, Y
Tsuruta, H
Yamaguchi, K
[J]. CHEMISTRY LETTERS, 1996, (10) : 875 - 876

← 1 2 3 4 →