Highly regioselective hydrogenolysis of bis(α-methylbenzyl)amine derivatives affected by the trifluoromethyl substituent on the aromatic ring

被引：37

作者：

Kanai, M ^{[1
]}

Yasumoto, M

Kuriyama, Y

Inomiya, K

Katsuhara, Y

Higashiyama, K

Ishii, A

机构：

[1] Cent Glass Co Ltd, Chem Res Ctr, Kawagoe, Saitama 3501151, Japan

[2] Hoshi Univ, Fac Pharmaceut Sci, Tokyo 1428501, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 07期

关键词：

D O I：

10.1021/ol034014w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The highly regloselective hydrogenolysis of bis(alpha-methylbenzyl)amine derivatives proceeded with influence not from the electronic effect but from the steric effect of the trifluoromethyl substituent on the aromatic ring to provide a practical asymmetric synthesis of trifluoromethylsubstituted alpha-phenylethylamines.

引用

页码：1007 / 1010

页数：4

共 20 条

[1]

ALVARO G, 2001, Patent No. 0125219

[2]

Armstrong H, 2001, WO, Patent No. 0100213

[3] Catalytic debenzylation. The effect of substitution on the strength of the O-benzyl and N-benzyl linkages [J].

Baltzly, R ;

Buck, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :1984-1992

[4]

BLOOM JD, 2000, Patent No. 0034269

[5] STERIC EFFECTS - A STUDY OF A RATIONALLY DESIGNED SYSTEM [J].

BOTT, G ;

FIELD, LD ;

STERNHELL, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) :5618-5626

[6] CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF N-CONTAINING NATURAL-PRODUCTS .4. A FACILE METHOD FOR THE ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE 1-(2-FLUOROPHENYL)-ETHYLAMINE [J].

BRINGMANN, G ;

GEISLER, JP .

JOURNAL OF FLUORINE CHEMISTRY, 1990, 49 (01) :67-73

[7] CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF N-CONTAINING NATURAL-PRODUCTS .1. ENANTIOMERICALLY PURE OXYGENATED 1-PHENYLETHYLAMINES FROM SUBSTITUTED ACETOPHENONES - BY REDUCTIVE AMINATION AND REGIOSPECIFIC BENZYLIC CLEAVAGE [J].

BRINGMANN, G ;

GEISLER, JP .

TETRAHEDRON LETTERS, 1989, 30 (03) :317-320

[8]

BRINGMANN G, 1990, LIEBIGS ANN CHEM, P795

[9]

BRINGMANN G, 1989, Patent No. 3819438

[10] A convenient asymmetric synthesis of alpha-1-arylalkylamines through the enantioselective hydrogenation of enamides [J].

Burk, MJ ;

Wang, YM ;

Lee, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5142-5143

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