Chiral induction controlled by aggregation of organometallics:: trifluoromethylated aminoalcohols for chiral ligands in Et2Zn alkylation of benzaldehyde

被引：25

作者：

Katagiri, T ^{[1
]}

Fujiwara, Y ^{[1
]}

Takahashi, S ^{[1
]}

Ozaki, N ^{[1
]}

Uneyama, K ^{[1
]}

机构：

[1] Okayama Univ, Dept Appl Chem, Okayama 7008530, Japan

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 09期

关键词：

D O I：

10.1039/b201238c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral induction in the reaction of Et2Zn with PhCHO by fluorinated chiral amino alcohols was correlated to the extent of aggregation of Et2Zn species, which was estimated by manometric study.

引用

页码：986 / 987

页数：2

共 39 条

[11] General syntheses of optically active α-trifluoromethylated amines via ring-opening reactions of N-benzyl-2-trifluoromethylaziridine [J].

Katagiri, T ;

Takahashi, M ;

Fujiwara, Y ;

Ihara, H ;

Uneyama, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7323-7329

[12] Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs [J].

Kitamura, M ;

Suga, S ;

Oka, H ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9800-9809

[13] ENANTIOMER RECOGNITION OF ASYMMETRIC CATALYSTS - THERMODYNAMIC PROPERTIES OF HOMOCHIRAL AND HETEROCHIRAL DIMERS OF THE METHYLZINC ALKOXIDE FORMED FROM DIMETHYLZINC AND ENANTIOMERIC 3-EXO-(DIMETHYLAMINO)ISOBORNEOL [J].

KITAMURA, M ;

SUGA, S ;

NIWA, M ;

NOYORI, R ;

ZHAI, ZX ;

SUGA, H .

JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (48) :12776-12781

[14] Asymmetric addition of dialkylzincs to benzaldehyde derivatives catalyzed by chiral β-amino alcohols.: Evidence for the monomeric alkylzinc aminoalkoxide as catalyst [J].

Kitamura, M ;

Oka, H ;

Noyori, R .

TETRAHEDRON, 1999, 55 (12) :3605-3614

[15] Homochiral and heterochiral dimers of the methylzinc alkoxide formed from dimethylzinc and enantiomeric 3-exo-(dimethylamino)isoborneol - Origin of the distinct differences in solution-phase behavior and crystal structures [J].

Kitamura, M ;

Yamakawa, M ;

Oka, H ;

Suga, S ;

Noyori, R .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (09) :1173-1181

[16] SELF AND NONSELF RECOGNITION OF ASYMMETRIC CATALYSTS - NONLINEAR EFFECTS IN THE AMINO ALCOHOL-PROMOTED ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].

KITAMURA, M ;

SUGA, S ;

NIWA, M ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (17) :4832-4842

[17] ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT [J].

KITAMURA, M ;

OKADA, S ;

SUGA, S ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4028-4036

[18]

KOPPENHOEFER B, 1988, ORG SYNTH, V66, P160

[19]

KOPPENHOEFER B, 1988, ORG SYNTH, V66, P151

[20] Utilization of industrial waste materials.: Part 14.: Synthesis of β-amino alcohols and thiols with a 2-azabicyclo[3.3.0]octane backbone and their application in enantioselective catalysis [J].

Kossenjans, M ;

Soeberdt, M ;

Wallbaum, S ;

Harms, K ;

Martens, J ;

Aurich, HG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (16) :2353-2365

← 1 2 3 4 →