Asymmetric conjugate addition of thiols to a 3-(2-alkenoyl)-2-oxazolidinone catalyzed by the DBFOX/Ph aqua complex of nickel(II) perchlorate

被引：151

作者：

Kanemasa, S ^{[1
]}

Oderaotoshi, Y ^{[1
]}

Wada, E ^{[1
]}

机构：

[1] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 37期

关键词：

D O I：

10.1021/ja991064g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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页码：8675 / 8676

页数：2

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共 19 条

[1] A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations [J].

Emori, E ;

Arai, T ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4043-4044

[2] ADDITION OF AROMATIC THIOLS TO CONJUGATED CYCLOALKENONES, CATALYZED BY CHIRAL BETA-HYDROXY AMINES - A MECHANISTIC STUDY ON HOMOGENEOUS CATALYTIC ASYMMETRIC-SYNTHESIS [J].

HIEMSTRA, H ;

WYNBERG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (02) :417-430

[3]

JONES DN, 1979, SULPHYR SELENIUM SIL, V3, P3

[4] Asymmetric cycloaddition reactions catalyzed by transition metal complexes - New guidelines for structural design of chiral catalyst [J].

Kanemasa, S ;

Oderaotoshi, Y .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1998, 56 (05) :368-376

[5] Temperature dependent 1H NMR study of the substrate complex derived from zinc(II) perchlorate, (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline), and 3-acetyl-2-oxazolidinone.: Evidence for octahedral structure of the substrate complex [J].

Kanemasa, S ;

Oderaotoshi, Y ;

Tanaka, J ;

Wada, E .

TETRAHEDRON LETTERS, 1998, 39 (41) :7521-7524

[6] Highly endo- and enantioselective asymmetric nitrone cycloadditions catalyzed by the aqua complex of 4,6-dibenzofurandiyl-2,2′-bis (4-phenyl-oxazoline)-nickel(II) perchlorate.: Transition structure based on dramatic effect of MS 4A on selectivities [J].

Kanemasa, S ;

Oderaotoshi, Y ;

Tanaka, J ;

Wada, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) :12355-12356

[7] Cationic aqua complexes of the C-2-symmetric trans-chelating ligand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline). Absolute chiral induction in Diels-Alder reactions catalyzed by water-tolerant enantiopure Lewis acids [J].

Kanemasa, S ;

Oderaotoshi, Y ;

Yamamoto, H ;

Tanaka, J ;

Wada, E ;

Curran, DP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6454-6455

[8] Transition-metal aqua complexes of 4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline).: Effective catalysis in Diels-Alder reactions showing excellent enantioselectivity, extreme chiral amplification, and high tolerance to water, alcohols, amines, and acids [J].

Kanemasa, S ;

Oderaotoshi, Y ;

Sakaguchi, S ;

Yamamoto, H ;

Tanaka, J ;

Wada, E ;

Curran, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3074-3088

[9] CONJUGATE ADDITION OF AMINES AND THIOLS TO (R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE - PREPARATION OF ENANTIOPURE N-ACYLIMINIUM ION PRECURSORS [J].

KOOT, WJ ;

HIEMSTRA, H ;

SPECKAMP, WN .

TETRAHEDRON-ASYMMETRY, 1993, 4 (08) :1941-1948

[10] Asymmetric construction of two contiguous stereocenters by diastereoface differentiating addition reaction of thiols to chiral imides: Formal synthesis of (+)-diltiazem [J].

Miyata, O ;

Shinada, T ;

Ninomiya, I ;

Naito, T .

TETRAHEDRON, 1997, 53 (07) :2421-2438