Enhanced diastereoselectivity of an ene hydroperoxidation reaction by confinement within zeolite Na-Y; a stereoisotopic study

被引：21

作者：

Stratakis, M ^{[1
]}

Kosmas, G ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, GR-71409 Iraklion, Greece

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 34期

关键词：

zeolite Na-Y; ene reactions; diastereoselection;

D O I：

10.1016/S0040-4039(01)01170-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ene reaction of singlet oxygen with the. chiral alkene 2-methyl-5-phenyl-2-hexene in solution is not regioselective and exhibits very poor diastereoselectivity (similar to 10% d.e.). Within thionin-supported zeolite Na-Y, significant enhancement of product regioselectivity and diastereoselectivity (up to 54% d.e.) was obtained. Higher diastereoselectivity is found if the reaction occurs at the twix relative to the twin methyl group. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：6007 / 6009

页数：3

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共 13 条

[1] The new skew and the established cis and gem regioselectivities in the ene reaction of trisubstituted olefins:: Comparison of the singlet oxygen, triazolinedione, and nitrosoarene enophiles [J].

Adam, W ;

Bottke, N ;

Krebs, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6791-6792

[2] Preparation of optically active allylic hydroperoxy alcohols and 1,3-diols by enzyme-catalyzed kinetic resolution and photooxygenation of chiral homoallylic alcohols [J].

Adam, W ;

Saha-Möller, CR ;

Schmid, KS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1431-1433

[3] New mechanistic and synthetic aspects of singlet oxygen chemistry [J].

Clennan, EL .

TETRAHEDRON, 2000, 56 (47) :9151-9179

[4] Photochemical reactions in the interior of a zeolite. Part 5: The origin of the zeolite induced regioselectivity in the singlet oxygen ene reaction [J].

Clennan, EL ;

Sram, JP .

TETRAHEDRON, 2000, 56 (36) :6945-6950

[5] Photochemistry of a tropolone ether and 2,2-dimethyl-1-(2H)-naphthalenones within a zeolite:: Enhanced diastereoselectivity via confinement [J].

Joy, A ;

Uppili, S ;

Netherton, MR ;

Scheffer, JR ;

Ramamurthy, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) :728-729

[6] Selective oxidation of olefins within organic dye cation-exchanged zeolites [J].

Li, XY ;

Ramamurthy, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10666-10667

[7] The Schenck ene reaction: Diastereoselective oxyfunctionalization with singlet oxygen in synthetic applications [J].

Prein, M ;

Adam, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (05) :477-494

[8] Energy transfer, proton transfer and electron transfer reactions within zeolites [J].

Ramamurthy, V ;

Lakshminarasimhan, P ;

Grey, CP ;

Johnston, LJ .

CHEMICAL COMMUNICATIONS, 1998, (22) :2411-2424

[9] Generation and reactivity of singlet oxygen within zeolites: Remarkable control of hydroperoxidation of alkenes [J].

Robbins, RJ ;

Ramamurthy, V .

CHEMICAL COMMUNICATIONS, 1997, (11) :1071-1072

[10] Organic transformations using zeolites and zeotype materials [J].

Sen, SE ;

Smith, SM ;

Sullivan, KA .

TETRAHEDRON, 1999, 55 (44) :12657-12698