β-isocupreidine-hexafluoroisopropyl acrylate method for asymmetric Baylis-Hillman reactions

被引：77

作者：

Nakano, A ^{[1
]}

Kawahara, S ^{[1
]}

Akamatsu, S ^{[1
]}

Morokuma, K ^{[1
]}

Nakatani, M ^{[1
]}

Iwabuchi, Y ^{[1
]}

Takahashi, K ^{[1
]}

Ishihara, J ^{[1
]}

Hatakeyama, S ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

关键词：

beta-isocupreidine; 1,1,1,3,3,3-hexafluoroisopropyl acrylate; organic catalysis;

D O I：

10.1016/j.tet.2005.09.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Key features of the beta-isocupreidine (beta-ICD)-catalyzed asymmetric Baylis-Hillman reaction of aldehydes with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) are presented. In addition, an improved method using azeotropically dried beta-ICD is described. (c) 0 2005 Elsevier Ltd. All rights reserved.

引用

页码：381 / 389

页数：9

共 25 条

[1] General acid-base catalysis in the reversible disproportionation reaction of N-chlorotaurine [J].

Antelo, JM ;

Arce, F ;

Calvo, P ;

Crugeiras, J ;

Ríos, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (10) :2109-2114

[2] Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction [J].

Balan, D ;

Adolfsson, H .

TETRAHEDRON LETTERS, 2003, 44 (12) :2521-2524

[3] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[4] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[5] Synthesis of oxazatwistanes and their homo- and bishomo-analogues from quinidine - Medium ring systems derived from cinchona alkaloids [J].

Braje, W ;

Frackenpohl, J ;

Langer, P ;

Hoffmann, HMR .

TETRAHEDRON, 1998, 54 (14) :3495-3512

[6]

Ciganek E., 1997, ORG REACTIONS, V51, P201

[7] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].

DREWES, SE ;

ROOS, GHP .

TETRAHEDRON, 1988, 44 (15) :4653-4670

[8] SYNTHESIS, RESOLUTION AND ASSIGNMENT OF ABSOLUTE-CONFIGURATION OF 2-(ALPHA-HYDROXY)ARYL ACRYLATE ESTERS [J].

DREWES, SE ;

EMSLIE, ND ;

FIELD, JS ;

KHAN, AA ;

RAMESAR, N .

TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :255-260

[9] REACTIONS WITH THIOETHOXIDE ION IN DIMETHYLFORMAMIDE .1. SELECTIVE DEMETHYLATION OF ARYL METHYL ETHERS [J].

FEUTRILL, GI ;

MIRRINGT.RN .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (08) :1719-&

[10] LITHIUM TRIETHYLBOROHYDRIDE REDUCTION OF ALKYL METHANESULFONATE ESTERS [J].

HOLDER, RW ;

MATTURRO, MG .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (12) :2166-2168

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