Linear Free-Energy Relationship Analysis of a Catalytic Desymmetrization Reaction of a Diarylmethane-bis(phenol)

被引：52

作者：

Gustafson, Jeffrey L. ^{[2
]}

Sigman, Matthew S. ^{[1
]}

Miller, Scott J. ^{[2
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

[2] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

STEREOCHEMISTRY; COMBINATORIAL; INDUCTION; DIPHENYLS; RATES; ACID;

D O I：

10.1021/ol100927m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Linear free-energy relationships have been found for enantioselectivity and various steric parameters in an enantioselective desymmetrization of symmetrical bis(phenol) substrates. The potential origin of this observation and the role of different steric parameters are discussed.

引用

页码：2794 / 2797

页数：4

共 34 条

[1] The stereochemistry of diphenyls and analogous compounds
Adams, R
Yuan, HC
[J]. CHEMICAL REVIEWS, 1933, 12 (02) : 261 - 338
[2] STEREOSELECTIVE ACYLATION OF RACEMIC SECONDARY ALCOHOLS WITH PHENYLTRIFLUOROMETHYLKETENE AS AN EXPERIMENTAL TEST OF STEREOCHEMICAL ANALOGY MODEL
ANDERS, E
RUCH, E
UGI, I
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (01): : 25 - 29
[3] Anslyn E. V., 2006, MODERN PHYS ORGANIC
[4] STERIC EFFECTS - A STUDY OF A RATIONALLY DESIGNED SYSTEM
BOTT, G
FIELD, LD
STERNHELL, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) : 5618 - 5626
[5] CHIRAL INDUCTION IN PHOTOCHEMICAL-REACTIONS .14. LINEAR FREE-ENERGY RELATIONSHIPS AS AN INSTRUMENT FOR THE PREDICTION OF EITHER DE VALUES OR CONFORMATION ENERGIES OF THE AUXILIARY IN THE DIASTEREOSELECTIVE PATERNO-BUCHI REACTION
BUSCHMANN, H
HOFFMANN, N
SCHARF, HD
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1429 - 1444
[6] THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY
BUSCHMANN, H
SCHARF, HD
HOFFMANN, N
ESSER, P
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) : 477 - 515
[7] Solvent effects on stereoselectivity: more than just an environment
Cainelli, Gianfranco
Galletti, Paola
Giacomini, Daria
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (04) : 990 - 1001
[8] STERIC EFFECTS .7. ADDITIONAL UPSILON CONSTANTS
CHARTON, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) : 2217 - 2220
[9] STERIC EFFECTS .2. BASE-CATALYZED ESTER HYDROLYSIS
CHARTON, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (13) : 3691 - 3693
[10] STERIC EFFECTS .1. ESTERIFICATION AND ACID-CATALYZED HYDROLYSIS OF ESTERS
CHARTON, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) : 1552 - 1556

← 1 2 3 4 →