CONFORMATIONAL ASPECTS OF SOME ASYMMETRIC DIELS-ALDER REACTIONS - A MOLECULAR MECHANICS PLUS POLARIZATION STUDY

被引：31

作者：

TORRENS, F

RUIZLOPEZ, M

CATIVIELA, C

GARCIA, JI

MAYORAL, JA

机构：

[1] UNIV NANCY 1,CHIM THEOR LAB,CNRS,URA 510,BP 239,F-54510 VANDOEUVRE NANCY,FRANCE

[2] UNIV ZARAGOZA,CSIC,DEPT QUIM ORGAN & QUIM FIS,INST CIENCIA MAT ARAGON,E-50009 ZARAGOZA,SPAIN

来源：

TETRAHEDRON | 1992年 / 48卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)90129-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The MM2 force field, improved by the inclusion of interacting induced dipole (ID) energies, is used to calculate the conformational preferences of three chiral dienophiles: Acrylate of (S)-ethyl lactate (1), N-acryloyl-L-phenylalanine methyl ester (2), and N-acryloyl-L-alanine methyl ester (3). The results obtained agree with the models previously proposed to account for the asymmetric induction obtained in the reaction of these dienophiles with cyclopentadiene.

引用

页码：5209 / 5218

页数：10

共 28 条

[21] STRUCTURAL CHARACTERISTICS OF THE CARBOXYLIC ESTER GROUP
SCHWEIZER, WB
DUNITZ, JD
[J]. HELVETICA CHIMICA ACTA, 1982, 65 (05) : 1547 - 1554
[22] Molecular refractivity and atomic interaction.
Silberstein, L.
[J]. PHILOSOPHICAL MAGAZINE, 1917, 33 (193-98) : 92 - 128
[23] MOLECULAR DYNAMICS SIMULATIONS WITH INTERACTION POTENTIALS INCLUDING POLARIZATION Development of a noniterative method and application to water
Straatsma, T. P.
McCammon, J. A.
[J]. MOLECULAR SIMULATION, 1990, 5 (3-4) : 181 - 192
[24] ARGOS, A VECTORIZED GENERAL MOLECULAR-DYNAMICS PROGRAM
STRAATSMA, TP
MCCAMMON, JA
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (08) : 943 - 951
[25] FREE-ENERGY THERMODYNAMIC INTEGRATIONS IN MOLECULAR-DYNAMICS SIMULATIONS USING A NONITERATIVE METHOD TO INCLUDE ELECTRONIC POLARIZATION
STRAATSMA, TP
MCCAMMON, JA
[J]. CHEMICAL PHYSICS LETTERS, 1990, 167 (03) : 252 - 254
[26] FREE-ENERGY EVALUATION FROM MOLECULAR-DYNAMICS SIMULATIONS USING FORCE-FIELDS INCLUDING ELECTRONIC POLARIZATION
STRAATSMA, TP
MCCAMMON, JA
[J]. CHEMICAL PHYSICS LETTERS, 1991, 177 (4-5) : 433 - 440
[27] TORRENS F, UNPUB
[28] (S)-PROLINE BENZYL ESTER AS CHIRAL AUXILIARY IN LEWIS ACID-CATALYZED ASYMMETRIC DIELS-ALDER REACTIONS
WALDMANN, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) : 6133 - 6136

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