Enantiomeric excesses and electronic chirality measure

被引：28

作者：

Bellarosa, L ^{[1
]}

Zerbetto, F ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 07期

关键词：

D O I：

10.1021/ja028646+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present an approach to measure the amount of chirality in the electronic wave function and apply it to the study of a set of asymmetric aminohydroxylation reactions. The correlation coefficient between the chirality measure and the enantiomeric excesses is larger than 0.9 and suggests that this phenomenological approach can be a valuable tool to investigate and, perhaps in the future, design asymmetric synthesis.

引用

页码：1975 / 1979

页数：5

共 16 条

[11] N-halocarbamate salts lead to more efficient catalytic asymmetric aminohydroxylation [J].

Li, GG ;

Angert, HH ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2813-2817

[12] Enhancement of enantiomeric excess by ligand distortion [J].

Lipkowitz, KB ;

Schefzick, S ;

Avnir, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6710-6711

[13] Computation of physical chirality: An assessment of orbital desymmetrization induced by common chiral auxiliaries [J].

Lipkowitz, KB ;

Gao, DQ ;

Katzenelson, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) :5559-5564

[14] A NEW TWIST TO MOLECULAR CHIRALITY - INTRINSIC CHIRALITY INDEXES [J].

OSIPOV, MA ;

PICKUP, BT ;

DUNMUR, DA .

MOLECULAR PHYSICS, 1995, 84 (06) :1193-1206

[15] Smaller substituents on nitrogen facilitate the osmium-catalyzed asymmetric aminohydroxylation [J].

Rudolph, J ;

Sennhenn, PC ;

Vlaar, CP ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2810-2813

[16] CONTINUOUS SYMMETRY MEASURES [J].

ZABRODSKY, H ;

PELEG, S ;

AVNIR, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7843-7851

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