Reactive-state spin-dependent diastereoselective photoisornerization of trans,trans-2,3-diphenylcyclopropane-1-carboxylic acid derivatives included in zeolites

被引：14

作者：

Sivaguru, J ^{[1
]}

Shichi, T ^{[1
]}

Ramamurthy, V ^{[1
]}

机构：

[1] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 24期

关键词：

D O I：

10.1021/ol026695l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric induction facilitated by a chiral auxiliary during the photoisomerization of trans, trans-2,3-diphenylcyclopropane derivatives depends on the medium (solution vs zeolite) and the reactive state (singlet vs triplet). Within zeolites, direct excitation most likely proceeds via a zwitterionic intermediate, while triplet sensitization most likely proceeds via a diradical intermediate.

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页码：4221 / 4224

页数：4

相关论文

共 17 条

[1] Use of chirally modified zeolites and crystals in photochemical asymmetric synthesis [J].

Chong, KCW ;

Sivaguru, J ;

Shichi, T ;

Yoshimi, Y ;

Ramamurthy, V ;

Scheffer, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2858-2859

[2] ASYMMETRIC INDUCTION DURING ENERGY TRANSFER [J].

HAMMOND, GS ;

COLE, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3256-&

[3] PHOTOSENSITIZED ISOMERIZATION INVOLVING SATURATED CENTERS [J].

HAMMOND, GS ;

TURRO, NJ ;

WYATT, P ;

DEBOER, CD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (12) :2532-&

[4] ARYLCYCLOPROPANE PHOTOCHEMISTRY - PHOTOCHEMICAL ADDITION OF HYDROXYLIC COMPOUNDS TO 1,2-DIARYLCYCLOPROPANES [J].

HIXSON, SS ;

GARRETT, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (15) :4872-4879

[5] ARYLCYCLOPROPANE PHOTOCHEMISTRY - PHOTOCHEMICAL ADDITION OF AMINES TO 1,2-DIARYLCYCLOPROPANES [J].

HIXSON, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (15) :4866-4871

[6]

HIXSON SS, 1979, ORG PHOTOCHEM, V4, P191

[7] STUDIES IN STEREOCHEMISTRY .45. ZWITTERIONIC TRANSITION-STATES IN EPIMERIZATION REACTIONS OF SUBSTITUTED CYCLOPROPANES [J].

HOWE, NE ;

YANKEE, EW ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (13) :4230-4237

[8] Photochemical C-C bond cleavage of 1,2-diarylcyclopropanes bearing an acetylphenyl group. Generation and observation of triplet 1,3-biradicals [J].

Ichinose, N ;

Mizuno, K ;

Otsuji, Y ;

Caldwell, RA ;

Helms, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3176-3184

[9] ENANTIODIFFERENTIATING CIS-TRANS PHOTOISOMERIZATIONS OF 1,2-DIARYLCYCLOPROPANES AND 2,3-DIPHENYLOXIRANE SENSITIZED BY CHIRAL AROMATIC ESTERS [J].

INOUE, Y ;

YAMASAKI, N ;

SHIMOYAMA, H ;

TAI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1785-1793

[10]

Mizuno K., 2000, J PHOTOCH PHOTOBIO C, V1, P167, DOI DOI 10.1016/S1389-5567(00)00011-3